DE1213856B - Process for the preparation of 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanes - Google Patents
Process for the preparation of 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanesInfo
- Publication number
- DE1213856B DE1213856B DESCH31569A DESC031569A DE1213856B DE 1213856 B DE1213856 B DE 1213856B DE SCH31569 A DESCH31569 A DE SCH31569A DE SC031569 A DESC031569 A DE SC031569A DE 1213856 B DE1213856 B DE 1213856B
- Authority
- DE
- Germany
- Prior art keywords
- diphenyl
- tert
- alkoxy
- aminopropanes
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 7
- 230000002048 spasmolytic effect Effects 0.000 description 5
- -1 1,1 - Diphenyl - 1 - methoxy - 3 - diethylaminopropane hydrochloride Chemical compound 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000812 cholinergic antagonist Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- LYWASOZKZYKPQR-UHFFFAOYSA-N [ethoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCC)C1=CC=CC=C1 LYWASOZKZYKPQR-UHFFFAOYSA-N 0.000 description 2
- IBNWKIKUJJNBKG-UHFFFAOYSA-N [methoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OC)C1=CC=CC=C1 IBNWKIKUJJNBKG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- DKZKNEZEUIHBKX-UHFFFAOYSA-N 3-methoxy-n,n-dimethyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCN(C)C)(OC)C1=CC=CC=C1 DKZKNEZEUIHBKX-UHFFFAOYSA-N 0.000 description 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
- QHHUCCOZVUZUSR-UHFFFAOYSA-N C=1C=CC=CC=1C([Na])C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C([Na])C1=CC=CC=C1 QHHUCCOZVUZUSR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WUIXMACUOWFWAA-UHFFFAOYSA-N [phenyl(propan-2-yloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(OC(C)C)C1=CC=CC=C1 WUIXMACUOWFWAA-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 1,1-Diphenyl-1-alkoxy-3-tert.-aminopropanen Um dem als Handelsprodukt bekannten Papaverin bezüglich der spasmolytischen Wirksamkeit überlegene Substanzen zu erhalten, wurden von A. C. K jaer und P. V. Petersen (Acta Chem. Scand.. Bd. 5, 1951, S. 1145) zunächst verschiedene 1,1 - Diphenyl -1- hydroxy - 3 - tert. - aminopropanderivate hergestellt, die jedoch durchweg keine spasmolytische Wirkung zeigten. Die gleichen Verfasser schlugen schließlich vor, die tert.-Hydroxygruppe ihrer Carbinole mit Hydroxyaceton zu veräthern. Der so erhaltene Acetonyl-(1,1-diphenyl-2 - methyl - 3 - dimethylamino) - propyläther besitzt zwar gute spasmolytische Wirkung, kommt aber wie die entsprechenden Ester für eine praktische Verwendung nicht in Frage, da er sich in wäßriger Lösung selbst bei Raumtemperatur schon nach einigen Stunden zersetzt.Process for the preparation of 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanes To papaverine, which is known as a commercial product, with regard to its spasmolytic effectiveness To obtain superior substances, A. C. K jaer and P. V. Petersen (Acta Chem. Scand. Vol. 5, 1951, p. 1145) initially various 1,1-diphenyl-1-hydroxy - 3 - tert. - aminopropane derivatives are produced, but none of them are spasmolytic Showed effect. The same authors eventually suggested the tertiary hydroxy group etherifying their carbinols with hydroxyacetone. The acetonyl- (1,1-diphenyl-2 - methyl - 3 - dimethylamino) - propyl ether has a good spasmolytic effect, but, like the corresponding esters, does not come into practical use Question, since it already settles in an aqueous solution even at room temperature after some Hours decomposed.
Es wurde nun gefunden, daß in überraschender Weise die 1,1- Diphenyl -1- alkoxy - 3 - tert. - aminopropane der allgemeinen Formel worin R1 einen niedermolekularen Alkylrest und R2 und R3 einen niedermolekularen Alkylrest oder R2 und R2 zusammen den Rest ~ CH2CW-O-CH2-CH2-bedeuten, und deren Salzen mit anorganischen und bzw. oder organischen Säuren sehr gute, dem Papaverin überlegene spasmolytische Wirksamkeit besitzen und darüber hinaus in Form der Salze, vorzugsweise als Hydrochlorid, in wäßriger Lösung praktisch unbegrenzt beständig sind.It has now been found that, surprisingly, the 1,1-diphenyl -1-alkoxy - 3 - tert. - aminopropane of the general formula where R1 is a low molecular weight alkyl radical and R2 and R3 are a low molecular weight alkyl radical or R2 and R2 together are the radical ~ CH2CW-O-CH2-CH2-, and their salts with inorganic and / or organic acids have very good spasmolytic activity superior to papaverine and, moreover, in the form of the salts, preferably as the hydrochloride, are practically unlimited in stability in aqueous solution.
Die bisher nicht beschriebenen 1,1-Diphenyl-1-alkoxy-3-tert.-aminopropane werden hergestellt, indem man Diphenyl-alkoxymethane mit einem Alkalimetall, vorzugsweise Kalium, in flüssigem Ammoniak in die entsprechenden Alkalimetallverbindungen der allgemeinen Formel worin Me Alkali bedeutet, überführt, die man anschließend mit einem Amin der allgemeinen Formel worin Y ein Halogenatom bedeutet, das vorzugsweise in einem inerten Lösungsmittel wie Ather gelöst ist, umsetzt und die erhaltenen Basen gegebenenfalls mit anorganischen und bzw. oder organischen Säuren in an sich bekannter Weise in die entsprechenden Salze überführt.The 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanes not previously described are prepared by converting diphenylalkoxymethanes with an alkali metal, preferably potassium, in liquid ammonia into the corresponding alkali metal compounds of the general formula wherein Me denotes alkali, which is then converted with an amine of the general formula in which Y denotes a halogen atom which is preferably dissolved in an inert solvent such as ether, and the bases obtained are converted into the corresponding salts, if appropriate with inorganic and / or organic acids, in a manner known per se.
Neben der bereits erwähnten, überlegenen spasmolytischen Wirksamkeit der erfindungsgemäßen Verbindungen war auch der glatte Reaktionsverlauf der geschilderten Synthese zur Herstellung der 1,1 - Diphenyl - 1 - alkoxy - 3 - tert. - aminopropane unerwartet, da nach E. B e rgm a n n und J. H a r v e y (Berichte der Deutschen Chemischen Gesellschaft, Bd. 62, 1929, S. 915) bekannt ist, daß bei Einwirkung von Natriumpulver auf Diphenyl-methoxymethan in ätherischer Lösung unter Abspaltung der Methoxygruppe als Natriummethylat Diphenyl-methylnatrium gebildet wird. In addition to the already mentioned, superior spasmolytic effectiveness of the compounds according to the invention was also the smooth course of the reaction as described Synthesis for the preparation of the 1,1 - diphenyl - 1 - alkoxy - 3 - tert. - aminopropane unexpected, because according to E. B e rgm a n n and J. H a r v e y (reports of the Germans Chemical Society, Vol. 62, 1929, p. 915) is known that when exposed to Sodium powder on diphenyl methoxymethane in an ethereal solution with cleavage the methoxy group is formed as sodium methylate diphenylmethylsodium.
Die Herstellung der als Ausgangsprodukte benötigten Diphenyl-alkoxymethane, für die im Rahmen der vorliegenden Erfindung kein Schutz begehrt wird, erfolgt in an sich bekannter Weise. The production of the diphenylalkoxymethanes required as starting materials, for which no protection is sought within the scope of the present invention, takes place in in a manner known per se.
40,3 g Diphenylbrommethan werden in einer Alkoholatlösung aus 130 ml Alkohol und 4,1 g Natrium 11/2 Stunden unter Rückfluß erhitzt. Nach dem Erkalten wird das dabei abgeschiedene Natriumbromid abgesaugt, das Filtrat mit Wasser verdünnt und mit z. B. Äthyläther extrahiert. Die abgetrennte Atherlösung wird mit Wasser gewaschen, über z. B. 40.3 g of diphenylbromomethane are dissolved in an alcoholate solution from 130 ml of alcohol and 4.1 g of sodium were refluxed for 11/2 hours. After cooling down the separated sodium bromide is suctioned off and the filtrate is diluted with water and with z. B. Ethyl ether extracted. The separated ether solution is mixed with water washed, over z. B.
Natriumsulfat getrocknet und bis zur Trockne eingedampft. Der verbleibende Rückstand wird im Vakuum destilliert. In fast quantitativer Ausbeute erhält man so Diphenyl-äthoxymethan vom Kp.1s 160 bis 161"C.Dried sodium sulfate and evaporated to dryness. The remaining one The residue is distilled in vacuo. One obtains in almost quantitative yield so diphenyl-ethoxymethane from bp 160 to 161 "C.
Andere Diphenyl-alkoxymethane können analog hergestellt werden, wobei dem Reaktionsgemisch auch ein inertes Verdünnungsmittel wie beispielsweise Benzol zugesetzt werden kann. So siedet das entsprechend hergestellte Diphenyl-isopropoxymethan bei Kp.14 155 bis 158"C. Other diphenylalkoxymethanes can be prepared analogously, with Add an inert diluent such as benzene to the reaction mixture can be added. The diphenylisopropoxymethane produced accordingly boils at bp 14 155 to 158 "C.
Beispiel 1 In 120 cm3 flüssigem Ammoniak werden in Gegenwart einer katalytischen Menge Eisennitrats der Formel Fe(NO3)3 9 H20 1,96 g (0,05 Mol) Kalium gelöst. Anschließend wird in die ammoniakalische Kaliumamidlösung eine Lösung aus 9,91 g (0,05 Mol) Methylbenzhydryläther und 50 ml wasserfreiem Äther unter Rühren eingetropft. Nach etwa 10 Minuten werden dem Reaktionsgemisch schließlich noch 5,65 g (0,0525 Mol) Dimethyl-aminoäthylchlorid, gelöst in 50 cm3 wasserfreiem Äther, zugetropft und in der Kälte noch so lange weitergerührt, bis die ursprünglich rostbraune Farbe des Reaktionsgemisches verschwunden ist. Danach wird das überschüssige Ammoniak nach Entfernung des Kühlbades unter Rühren verdampft, wobei gleichzeitig etwa 50 ml Äther zugetropft werden. In das Reaktionsgemisch wird anschließend Wasser eingerührt, die sich abscheidende Ätherschicht abgetrennt, mit Wasser neutral gewaschen und schließlich mit Kaliumcarbonat getrocknet. Der filtrierten Ätherlösung wird nun ätherische Salzsäure zugesetzt, wobei in etwa 500/obiger Ausbeute das Hydrochlorid des 1,1- Diphenyl - 1- methoxy - 3 - dimethylaminopropans ausfällt, das nach Abtrennung im Vakuumtrockenschrank bei 600 C über Natriumhydroxyd getrocknet wird. F. 210 bis 212"C aus Methanol-Äther. Example 1 In 120 cm3 of liquid ammonia in the presence of a catalytic amount of iron nitrate of the formula Fe (NO3) 3 9 H20 1.96 g (0.05 mol) potassium solved. A solution is then made into the ammoniacal potassium amide solution 9.91 g (0.05 mol) of methylbenzhydryl ether and 50 ml of anhydrous ether with stirring dripped in. After about 10 minutes, the reaction mixture finally becomes 5.65 g (0.0525 mol) of dimethylaminoethyl chloride, dissolved in 50 cm3 of anhydrous ether, added dropwise and kept stirring in the cold until the originally rusty brown Color of the reaction mixture has disappeared. After that, the excess ammonia evaporated after removal of the cooling bath with stirring, at the same time about 50 ml of ether are added dropwise. Water is then stirred into the reaction mixture, the separating ether layer separated, washed neutral with water and finally dried with potassium carbonate. The filtered ether solution is now ethereal hydrochloric acid added, with the hydrochloride in about 500 / above yield of the 1,1-diphenyl-1-methoxy-3-dimethylaminopropane which precipitates after separation is dried in a vacuum drying cabinet at 600 C over sodium hydroxide. F. 210 to 212 "C from methanol-ether.
In analoger Weise werden folgende Verbindungen hergestellt: 1,1 - Diphenyl - 1 - methoxy - 3 - diäthylaminopropan-hydrochlorid, F. 154 bis 155"C; 1, 1-Diphenyl- 1-äthoxy-3-dimethylaminopropanhydrochlorid, F. 200 bis 201"C; 1,1- Diphenyl -1- äthoxy -3- morpholinopropanhydrochlorid, F. 214 bis 215"C (Zersetzung); 1,1 - Diphenyl - 1 - isopropoxy - 3 - morpholinopropan-hydrochlorid, F. 197 bis 199"C (Zersetzung). The following compounds are made in an analogous manner: 1,1 - Diphenyl - 1 - methoxy - 3 - diethylaminopropane hydrochloride, m.p. 154 to 155 "C; 1, 1-diphenyl- 1-ethoxy-3-dimethylaminopropane hydrochloride, m.p. 200 to 201 "C; 1,1- Diphenyl -1- ethoxy -3- morpholinopropane hydrochloride, mp 214 to 215 "C (decomposition); 1,1 - Diphenyl - 1 - isopropoxy - 3 - morpholinopropane hydrochloride, F. 197 bis 199 "C (decomposition).
Beispiel 2 In 200 ml flüssigem Ammoniak werden 2,94 g Kalium gelöst. Man wartet, bis die blaue Farbe der Lösung verschwunden ist und tropft dann 15,9 g Äthylbenzhydryläther in 80 ml wasserfreiem Äther unter Rühren zu. Nach etwa 20 Minuten werden 11,3 g 2-Morpholino-1-chloräthan in 70 ml Äther gelöst und in die Mischung getropft. Man arbeitet gemäß Beispiel 1 weiter und erhält 1,1-Diphenyl-1 - äthoxy - 3 - morpholinopropan - hydrochlorid, F. 214 bis 215"C (Zersetzung), in 470/oiger Ausbeute. Example 2 2.94 g of potassium are dissolved in 200 ml of liquid ammonia. One waits for the blue color of the Solution has disappeared and then drips 15.9 g of ethyl benzhydryl ether in 80 ml of anhydrous ether with stirring. After about 20 Minutes 11.3 g of 2-morpholino-1-chloroethane are dissolved in 70 ml of ether and poured into the Mixture dripped. The procedure of Example 1 is continued and 1,1-diphenyl-1 is obtained - ethoxy - 3 - morpholinopropane hydrochloride, F. 214 to 215 "C (decomposition), in 470% yield.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH31569A DE1213856B (en) | 1962-06-02 | 1962-06-02 | Process for the preparation of 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH31569A DE1213856B (en) | 1962-06-02 | 1962-06-02 | Process for the preparation of 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1213856B true DE1213856B (en) | 1966-04-07 |
Family
ID=7432151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH31569A Pending DE1213856B (en) | 1962-06-02 | 1962-06-02 | Process for the preparation of 1,1-diphenyl-1-alkoxy-3-tert.-aminopropanes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1213856B (en) |
-
1962
- 1962-06-02 DE DESCH31569A patent/DE1213856B/en active Pending
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