CH481875A - Process for the preparation of a new amine - Google Patents
Process for the preparation of a new amineInfo
- Publication number
- CH481875A CH481875A CH1257365A CH1257365A CH481875A CH 481875 A CH481875 A CH 481875A CH 1257365 A CH1257365 A CH 1257365A CH 1257365 A CH1257365 A CH 1257365A CH 481875 A CH481875 A CH 481875A
- Authority
- CH
- Switzerland
- Prior art keywords
- propane
- hydrolysis
- hydroxy
- formula
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001412 amines Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- -1 hydroxy-3- (o-propargyloxyphenoxy) propane Chemical compound 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- FYOGTFROMBUNKU-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(2-prop-2-ynoxyphenoxy)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC#C FYOGTFROMBUNKU-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- XSFWCIBEJZADAF-UHFFFAOYSA-N 2-prop-2-ynoxyphenol Chemical compound OC1=CC=CC=C1OCC#C XSFWCIBEJZADAF-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000208011 Digitalis Species 0.000 description 1
- 206010015856 Extrasystoles Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000000418 Premature Cardiac Complexes Diseases 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines neuen Amins
Gegenstand der Erfindung ist ein Verfahren zur Herstellung des l-Isopropylamino-2-hydroxy-3-(o-propafgyloxy- phe.noxy)-propans der Formel
EMI1.1
oder seiner Salze.
Die neue Verbindung besitzt wertvolle pharmakologische Eigenschaften. Inisbesondere bewirkt sie eine Hemmung adrenergischer ss-Rezeptoren. So hemmt sie z. B. an der mit Dial narkotiselerben Katze oder am wachen Hund durch Isoproterenol hervorgerufene Blut- drucksenkungen in Dosen von 0,01 bis 1 mg/kg i. v. oder 2 bis 3 mg/kg p. o. Sie ist inl der Lage, digitalisinduzierte Extrasystolen zu unterdrücken, wie z. B. aus Expert- mentez mit einer Dosis von 0, 3 bis 1 mg/kg i. v. am narkotisierten Hund hervorgeht.
Die Verbindung kann dementsprechend bei Herz-und Kreislauferkrankungen als Medikament angewendle, t werden.
Das erfindungsgemässe Verfahren zur Herstellung der neuen Verbindungen ist dadurch gekennzeichnet, dass man in einem l-Isopropylamino-2-hydroxy-3-(o-pro- pargyloxy-phenoxy)-propan oder einem Salz davon, das am Stickstoffatom und/oder an der 2-Hydroxylgruppe je einen einwertigen oder zusammen einen zweiwertigen durch Hydrolyse abspaltbaren Rest aufweist, diesen Rest durch Hydrolyse abspaltet. Solche Reste sind z. B.
Acylreste von Carbonsäure, wie niedere Alianoylreste, z. B. der Acetylrest. Verbindiungen mit durch Hydrolyse abspaltbaren Resten sind z. B. auch die der Formel 11
EMI1.2
worin X fUr die Carbonylgruppe odeur fur eine Alkyliden grappe steht.
Die Hydrolyse kann in üblicher Weise vorgenommen werden. Die Hydrolyse einer Verbindung der Formel II, worin X fur eine Alkylidengruppe stehEt, kann in saurer Lösung durchgeführt werden.
Die Ausgangsstoffe sind bekann, t oder können nach an sich bekannten Methoden gewonnen werden, z. B. dadurch, dal3 man o-Propargyloxy-phenol mit einer Verbindung der Formel
EMI1.3
umsetzt, wobei X die oben genannte Bedeutung hat und Z eine reaktionsfähig veresterbe HydXroxylgruppe, vor allem ein Halogenatom, wie Chlor-oder Bromatom, darstellt.
Je nach den Verfahrensbedingungen und Ausgangsstoffen kann man den Endstoff in freier Form oder in der ebenfalls in d4Dr Erfindung inbegriffenen Form seiner Salze erhalten. Die Salze des Endstoffs können in an sioh bekannter Weise, z. B. mit Alkalien oder Ionenaustauschern, in die freie Base übergeführt werden.
Von der letzteren lassen sich durch Umsetzung mit organ, ischen oder anorganischen Saurez, insbesondere solchen, die zur Bildung von therapeutisch verwendL baren Salzen geeignet sind, Salze gewinnen.
Als solche Säuren seien beispielsweise genannt : Halogenwasserstoff- säuren, Schwefelsäuren, Phosphorsäuren, Salpetersäure, Perchlorsaure, aliphatische, alicyclische, aromatische oder heterocyclische Carbon-oder Sulfonsäuren, wie Ameisen-, Essig-, Propion-, BerDstein-, Glykol-, Milch, Apfel-, Wein-, Zitronen-, Ascorbin-, Malein-, Hydroxy maleinW oder Brenztraubensäure ;
Phenylessig-, Benzol-, p-Aminobenzoe-, Anthranil ;, p-Hydroxybenzoe-, Salicyloder p-Aminosalicylsäure, Embonsäure, Methansulfon-, Äthansulfon-, Hydroxyäthansulfon-, Äthylensulfonsäure ; Halogenbenzolsulfon-, Toluolsulfon-, Naphthalinsulfon- saure oder Sulfanilsäure ; Methionin, Tryptophan, Lysin oder Arginin.
Diese oder andere Salze der neuen Verbindung, wie z. B. die Pikrate, können auch zur Reinigung der erhaltenen freien Base dienen, indem man die freie Base in Salze überführt, d, iese abtrennt und aus den Salzen wiederum die Base freimachlt. Infolge der engin Beziehungen zwischen der neuen Verbindung in freier Forum und in Form ilhrer Salze sind im vorausgegangenen und nachfolgend untor der freien Base sinn- und zweck mässig, gegebenenfalls auch die entsprechenden Salze zu verstehen.
Die neue Verbindung kann als Racemat oder in Form der Antipoden vorliegen. Das Racemat lässt sich in üblicher Weise in die Antipoden zerlegen.
Die neue Verbindung kann z. B. in Form pharmazeutischer Präparate Verwendung finden, welche sie in freier Form oder gegebenenfalls in) Form ihrer Salve in Mischung mit einem für die enterale oder parenterale Applikation geeigneten pharmazeutischen organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten.
In den folgenden Beispielen sind die Temperaturen in Celsiusgradent angegeben.
Beispiel 1
10,0 g 3-Isopropyl-5-(o-propargyloxy-phenoxymethyl3- oxazolidinon-(2) werden während 15 Minuten mit 50 ml lOn Natron lauge unter Rühren auf 120 erhitzt. Hierauf wird mit 100 ml Wasser versetzt, mit 5n Salzsäure angesäuert und mit Äther extrahiert. Die wässrige Masse stellt man mit Natronlauge alkalisch und extrahiert mit Äther. Nach dem Trocknen und Eindampfen des Lösungsmittels verbleibt das 1-Isopropylamina-2 hydroxy-3- (o-propargyloxy- phenoxy)-propan der Formel
EMI2.1
das bei 48 bis 52 sch-milzt.
Das Hydrochlorid der Verbindung schmilzt bei 96 bis 97 .
Beispiel 2
1 g 1-(N-Acetyl-isopropylamino)-2-acetoxy-(3-(opropargyloxy-phenoxy)-propan wird in 7 ml absolutem Alkohol und 3,5 ml 5n Natronlauge während 7 Stunden am Rückfluss gekocht. Die Reaktionslösung wird im Vakuum eingeengt Den Hindampfrückstand versetzt man mit Wasser und schüttelt mit Ather aus. Nach Eindampfen der getrockneten Ätherlösung erhält man als Rückstand das l-Isopropylamino-2-hyd, roxy-3-(o-pro- pargyloxy-phenoxy)-propan der Formel
EMI2.2
dessen Hydzochlorid bei 96 bis 97 schmilzt.
Beispiel 3
Zu einer Lösung von 5, 0 g 3-Isopropyl-5-(o-propargyloxy-phenoxymethyl)-oxazolidin in 50 ml Athanol gibt man 25 ml 2n Salzsäure und erwärmt eine Stunde auf 70 . anschliessend wird der Alkohol abdestilliert und den Rückstand versetzt man mit 75 ml 2n Natronlauge. Es sche) idet sich ein Öl ab, das mit Ather extrahiert wird. Nach dem Trocknen und Eindampfen des Athers bleibt das 1-Isopropylamino-2-hydroxy-3-(o-propargyl oxy-phenoxy) *propan dler Formel
EMI2.3
dessen Hydrochlorid bei 96 bis 97 schmilzt, zurück.
Process for the preparation of a new amine
The invention relates to a process for the preparation of l-isopropylamino-2-hydroxy-3- (o-propafgyloxyphe.noxy) propane of the formula
EMI1.1
or its salts.
The new compound has valuable pharmacological properties. In particular, it inhibits adrenergic ss receptors. So it inhibits z. B. isoproterenol-induced blood pressure reductions in doses of 0.01 to 1 mg / kg i in cats that are anesthetized with dial or in the awake dog. v. or 2 to 3 mg / kg p. o. It is able to suppress digitalis-induced extrasystoles, such as B. from Expert mentez with a dose of 0.3 to 1 mg / kg i. v. on the anesthetized dog.
The compound can accordingly be used as a medicament in cardiovascular diseases.
The inventive method for the preparation of the new compounds is characterized in that in a l-isopropylamino-2-hydroxy-3- (o-propargyloxy-phenoxy) propane or a salt thereof, which is on the nitrogen atom and / or on the 2-hydroxyl group each has a monovalent or together a bivalent radical which can be split off by hydrolysis, this radical splits off by hydrolysis. Such residues are e.g. B.
Acyl radicals of carboxylic acid, such as lower alianoyl radicals, e.g. B. the acetyl radical. Compounds with residues that can be split off by hydrolysis are z. B. also those of Formula 11
EMI1.2
where X stands for the carbonyl group or for an alkylidene group.
The hydrolysis can be carried out in the usual way. The hydrolysis of a compound of the formula II in which X is an alkylidene group can be carried out in acidic solution.
The starting materials are known or can be obtained by methods known per se, e.g. B. by dal3 one o-propargyloxy-phenol with a compound of the formula
EMI1.3
reacted, where X has the meaning given above and Z is a reactive esterifying hydroxyl group, especially a halogen atom, such as chlorine or bromine atom.
Depending on the process conditions and starting materials, the end product can be obtained in free form or in the form of its salts, which is also included in d4Dr invention. The salts of the end product can be used in a manner known per se, e.g. B. with alkalis or ion exchangers, are converted into the free base.
Salts can be obtained from the latter by reaction with organic, inorganic or inorganic acid ore, in particular those which are suitable for the formation of therapeutically useful salts.
Examples of such acids are: hydrohalic acids, sulfuric acids, phosphoric acids, nitric acid, perchloric acid, aliphatic, alicyclic, aromatic or heterocyclic carboxylic or sulphonic acids, such as formic, acetic, propionic, berdstein, glycol, milk, apple -, tartaric, citric, ascorbic, maleic, hydroxy maleinW or pyruvic acid;
Phenyl acetic, benzene, p-aminobenzoic, anthranil, p-hydroxybenzoic, salicylic or p-aminosalicylic acid, emboxylic acid, methanesulphonic, ethanesulphonic, hydroxyethanesulphonic, ethylene sulphonic acid; Halobenzenesulphonic, toluenesulphonic, naphthalenesulphonic acid or sulphanilic acid; Methionine, tryptophan, lysine or arginine.
These or other salts of the new compound, such as. B. the picrates, can also be used to purify the free base obtained by converting the free base into salts, d, separating these and in turn frees the base from the salts. As a result of the close relationship between the new compound in the free forum and in the form of its salts, it is sensible and expedient to understand the corresponding salts in the preceding and following with the free base.
The new compound can be present as a racemate or in the form of the antipodes. The racemate can be broken down into the antipodes in the usual way.
The new connection can e.g. B. in the form of pharmaceutical preparations are used, which they contain in free form or optionally in the form of their salve mixed with a pharmaceutical organic or inorganic, solid or liquid carrier material suitable for enteral or parenteral administration.
In the following examples the temperatures are given in degrees Celsius.
example 1
10.0 g of 3-isopropyl-5- (o-propargyloxy-phenoxymethyl-3-oxazolidinone- (2) are heated for 15 minutes with 50 ml of 10N sodium hydroxide solution while stirring to 120. 100 ml of water are then added and the mixture is acidified with 5N hydrochloric acid and extracted with ether. The aqueous mass is made alkaline with sodium hydroxide solution and extracted with ether. After drying and evaporation of the solvent, the 1-isopropylamine-2-hydroxy-3- (o-propargyloxyphenoxy) propane of the formula remains
EMI2.1
that melts at 48 to 52.
The compound's hydrochloride melts at 96 to 97.
Example 2
1 g of 1- (N-acetyl-isopropylamino) -2-acetoxy- (3- (opropargyloxy-phenoxy) -propane is refluxed in 7 ml of absolute alcohol and 3.5 ml of 5N sodium hydroxide solution for 7 hours The vapor residue is mixed with water and extracted with ether. After evaporation of the dried ether solution, the residue obtained is 1-isopropylamino-2-hyd, roxy-3- (o-propargyloxy-phenoxy) -propane of the formula
EMI2.2
its hydrochloride melts at 96 to 97.
Example 3
25 ml of 2N hydrochloric acid are added to a solution of 5.0 g of 3-isopropyl-5- (o-propargyloxy-phenoxymethyl) -oxazolidine in 50 ml of ethanol and the mixture is warmed to 70 for one hour. the alcohol is then distilled off and the residue is treated with 75 ml of 2N sodium hydroxide solution. An oil separates out and is extracted with ether. After drying and evaporation of the ether, the 1-isopropylamino-2-hydroxy-3- (o-propargyl oxy-phenoxy) * propane remains of the formula
EMI2.3
whose hydrochloride melts at 96 to 97, back.
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1210669A CH481874A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
| CH1210269A CH481873A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
| CH1257365A CH481875A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
| ES0320749A ES320749A1 (en) | 1964-12-17 | 1965-12-15 | Procedure for the obtaining of 1-isopropilamino - 2-hidroxi-3- (o-propargiloxi-fenoxi) - propane. (Machine-translation by Google Translate, not legally binding) |
| DK644665AA DK117065B (en) | 1964-12-17 | 1965-12-16 | Analogous process for the preparation of 1-isopropylamino-2-hydroxy-3- (o-propargyloxy-phenoxy) -propane or salts thereof. |
| AT337067A AT266083B (en) | 1965-09-09 | 1965-12-16 | Process for the preparation of the new 1-isopropylamino-2-hydroxy-3- (o-propargyloxy-phenoxy) -propane and its salts |
| SE16310/65A SE338771B (en) | 1964-12-17 | 1965-12-16 | |
| NL6516433A NL6516433A (en) | 1964-12-17 | 1965-12-16 | |
| SU1493609A SU363242A3 (en) | 1965-09-09 | 1965-12-16 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1257365A CH481875A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH481875A true CH481875A (en) | 1969-11-30 |
Family
ID=4384285
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1257365A CH481875A (en) | 1964-12-17 | 1965-09-09 | Process for the preparation of a new amine |
| CH1210669A CH481874A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
| CH1210269A CH481873A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1210669A CH481874A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
| CH1210269A CH481873A (en) | 1965-09-09 | 1965-09-09 | Process for the preparation of a new amine |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT266083B (en) |
| CH (3) | CH481875A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008711A1 (en) * | 1978-08-15 | 1980-03-19 | Smithkline Beckman Corporation | A method of preparing a 2-hydroxy-3-isopropyl or a 2-hydroxy-3-tert-butylaminopropyl aromatic ether |
-
1965
- 1965-09-09 CH CH1257365A patent/CH481875A/en not_active IP Right Cessation
- 1965-09-09 CH CH1210669A patent/CH481874A/en not_active IP Right Cessation
- 1965-09-09 CH CH1210269A patent/CH481873A/en not_active IP Right Cessation
- 1965-12-16 AT AT337067A patent/AT266083B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008711A1 (en) * | 1978-08-15 | 1980-03-19 | Smithkline Beckman Corporation | A method of preparing a 2-hydroxy-3-isopropyl or a 2-hydroxy-3-tert-butylaminopropyl aromatic ether |
Also Published As
| Publication number | Publication date |
|---|---|
| AT266083B (en) | 1968-11-11 |
| CH481873A (en) | 1969-11-30 |
| CH481874A (en) | 1969-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |