DE1119287B - Process for the preparation of blood pressure-effective secondary amines - Google Patents
Process for the preparation of blood pressure-effective secondary aminesInfo
- Publication number
- DE1119287B DE1119287B DEF28066A DEF0028066A DE1119287B DE 1119287 B DE1119287 B DE 1119287B DE F28066 A DEF28066 A DE F28066A DE F0028066 A DEF0028066 A DE F0028066A DE 1119287 B DE1119287 B DE 1119287B
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- preparation
- blood pressure
- tert
- 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 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000003335 secondary amines Chemical class 0.000 title claims description 4
- 230000036772 blood pressure Effects 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- -1 aryl sulfonic acid esters Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002262 Schiff base Substances 0.000 claims 1
- 150000004753 Schiff bases Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- LGAJYTCRJPCZRJ-UHFFFAOYSA-N 2-bromopentane Chemical compound CCCC(C)Br LGAJYTCRJPCZRJ-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- SGRBRAQXECVTBV-UHFFFAOYSA-N 2-methyl-n-propan-2-ylbutan-2-amine Chemical compound CCC(C)(C)NC(C)C SGRBRAQXECVTBV-UHFFFAOYSA-N 0.000 description 1
- ZWXQPERWRDHCMZ-UHFFFAOYSA-N 2-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)NC(C)(C)C ZWXQPERWRDHCMZ-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- 208000005400 Synovial Cyst Diseases 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AYHWQTQILBGWRN-UHFFFAOYSA-N butan-2-yl 4-methylbenzenesulfonate Chemical compound CCC(C)OS(=O)(=O)C1=CC=C(C)C=C1 AYHWQTQILBGWRN-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RRYYENPEMDHYLQ-UHFFFAOYSA-N n-tert-butylbutan-2-amine Chemical compound CCC(C)NC(C)(C)C RRYYENPEMDHYLQ-UHFFFAOYSA-N 0.000 description 1
- SZAGYXMYNOXHSN-UHFFFAOYSA-N n-tert-butylpentan-3-amine Chemical compound CCC(CC)NC(C)(C)C SZAGYXMYNOXHSN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- SLMCDJBSBDYBAX-UHFFFAOYSA-N pentan-3-yl 4-methylbenzenesulfonate Chemical compound CCC(CC)OS(=O)(=O)C1=CC=C(C)C=C1 SLMCDJBSBDYBAX-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
F28066IVb/12qF28066IVb / 12q
BEKANNTMACHUNG DER ANMELDUNG UNDAUSGABE DER AUSLEGESCHRIFT: 14. DEZEMBER 1961NOTICE THE REGISTRATION AND ISSUE OF EDITORIAL: DECEMBER 14, 1961
Es wurde gefunden, daß sekundäre Amine der allgemeinen FormelIt has been found that secondary amines of the general formula
CH,CH,
R —CH2-C —NH-R —CH 2 -C —NH-
CH3 CH 3
,R', R '
R"R "
sich durch ihre starke blutdrucksenkende und ganglienblockierende Wirkung auszeichnen. In der Formel bedeutet R Wasserstoff oder eine gerade oder verzweigte Alkylgruppe mit 1 bis 4 Kohlenstoffatomen, R' einen Alkylrest mit 1 bis 3 Kohlenstoffatomen und R" einen gesättigten oder ungesättigten Alkylrest mit 1 bis 3 Kohlenstoffatomen, der durch Hydroxylgruppen substituiert sein kann.are characterized by their strong antihypertensive and ganglion-blocking effect. In the formula means R is hydrogen or a straight or branched alkyl group with 1 to 4 carbon atoms, R 'is one Alkyl radical with 1 to 3 carbon atoms and R ″ a saturated or unsaturated alkyl radical with 1 to 3 Carbon atoms, which can be substituted by hydroxyl groups.
Für die Herstellung der erfindungsgemäß erhältlichen Amine kann man z. B. reaktionsfähige Halogenwasserstoffsäure-, Alkyl- oder Arylsulfonsäureester von Alkoholen der FormelFor the preparation of the amines obtainable according to the invention you can, for. B. reactive hydrohalic acid, Alkyl or aryl sulfonic acid esters of alcohols of the formula
ho—ch:high:
-R'-R '
1R" 1 R "
mit primären Aminen der Formelwith primary amines of the formula
R — CH2 — C(CH3)2 — NH2 R - CH 2 - C (CH 3 ) 2 - NH 2
in an sich bekannter Weise umsetzen.
Ferner kann man an Schiffsche Basen der Formelimplement in a manner known per se.
Furthermore, one can use Schiff's bases of the formula
R — CH2 — C(CHs)2 -N = CH-R'
R — CH2 — C(CH3)2 — N = CH — R"R - CH 2 - C (CHs) 2 -N = CH-R '
R - CH 2 - C (CH 3 ) 2 - N = CH - R "
Grignardverbindungen anlagern und die Produkte anschließend hydrolysieren.Add Grignard compounds and then hydrolyze the products.
Die erfindungsgemäß erhaltenen sekundären tert.-Alkylamine sind farblose Flüssigkeiten, die sich im Vakuum ohne Zersetzung destillieren lassen und die in organischen Lösungsmitteln löslich sind. Sie bilden mit anorganischen oder organischen Säuren gut kristallisierte, beständige Salze, die sich in Wasser lösen.The secondary tert-alkylamines obtained according to the invention are colorless liquids which are in the Allow vacuum to distill without decomposition and which are soluble in organic solvents. they form stable salts, well crystallized with inorganic or organic acids, which dissolve in water to solve.
73 g tert.-Butylamin werden mit 172 g Isopropyljodid
im Autoklav zuerst 6 Stunden auf 150° C und dann 6 Stunden auf 2000C erhitzt. Man löst den festgewordenen
Autoklaveninhalt in 250 ml Wasser, filtriert ab, setzt die Base aus der wäßrigen Lösung
mit konzentrierter Natronlauge in Freiheit und äthert aus. Nach Fraktionierung der ätherischen Lösung
Verfahren zur Herstellung
blutdruckwirksamer sekundärer Amine73 g of tert-butylamine are heated to 200 0 C and 172 g of isopropyl iodide in the first autoclave 6 hours at 150 ° C and then 6 hours. The solidified contents of the autoclave are dissolved in 250 ml of water, filtered off, the base is released from the aqueous solution with concentrated sodium hydroxide solution and left with ether. After fractionation of the essential solution method of preparation
blood pressure acting secondary amines
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,
Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft,
Leverkusen-Bayerwerk
Dr. Rudolf Hiltmann, Dr. Hartmund Wollweber,Dr. Rudolf Hiltmann, Dr. Hartmund Wollweber,
Dr. Wolfgang Wirth, Wuppertal-Elberfeld,
und Dr. Rudolf Gösswald, Wuppertal-Vohwinkel,
sind als Erfinder genannt wordenDr. Wolfgang Wirth, Wuppertal-Elberfeld,
and Dr. Rudolf Gösswald, Wuppertal-Vohwinkel,
have been named as inventors
erhält man 53 g tert.-Butylisopropylamin vom Kp.76O 98 bis 990C.is obtained 53 g of tert-butylisopropylamine from Kp. 76o 98 to 99 0 C.
Zur Überführung in das Hydrochlorid löst man dasTo convert it into the hydrochloride, this is dissolved
tert-Butylisopropylamin in Äther, versetzt mit der berechneten Menge ätherischer Salzsäure, filtriert ab und kristallisiert aus Methyläthylketon um. F. 196 bis 197° C.tert-Butylisopropylamine in ether, mixed with the calculated amount of ethereal hydrochloric acid, filtered off and recrystallized from methyl ethyl ketone. F. 196 up to 197 ° C.
73 g tert.-Butylamin und 130 g p-Toluolsulfosäure-3-pentylester werden 24 Stunden im Autoklav auf 100° C erhitzt. Nach Erkalten löst man den Inhalt des Autoklavs in wenig Wasser, macht mit Natronlauge stark alkalisch und treibt das Basengemisch mit Wasserdampf über. Aus dem Destillat trennt man das Öl ab, trocknet mit festem Kaliumhydroxyd und destilliert an einer 50-cm-Kolonne. Nach einem Vorlauf von tert-Butylamin erhält man 23,1 g N-tert.-Butyl-3-pentylamin vom Kp. 145°C; Hydrochlorid Schmp. 229,5 bis 230° C.73 g of tert-butylamine and 130 g of p-toluenesulfonic acid 3-pentyl ester are heated to 100 ° C in an autoclave for 24 hours. After cooling down, the content of the Autoclave in a little water, makes strongly alkaline with sodium hydroxide solution and drives the base mixture with it Water vapor over. The oil is separated off from the distillate, dried with solid potassium hydroxide and distilled on a 50 cm column. After a first run of tert-butylamine, 23.1 g of N-tert-butyl-3-pentylamine are obtained of bp 145 ° C; Hydrochloride m.p. 229.5 to 230 ° C.
Der durch Umsetzen von Pentan-3-ol mit p-Toluolsulfonylchlorid in Pyridin erhältliche p-Toluolsulfosäure-3-pentylester ist kristallisiert und wird ohne weitere Reinigung eingesetzt.That by reacting pentan-3-ol with p-toluenesulfonyl chloride 3-pentyl p-toluenesulfonate obtainable in pyridine has crystallized and is used without further purification.
Nach dem gleichen Arbeitsverfahren werden aus 60 g p-Toluolsulfonsäure-2-butylester und 50 g tert.-Butylamin 7 g N-tert.-Butyl-2-butylamin (Kp.75O 115 bis 117°C; Hydrochlorid F. 173 bis 174°C) gewonnen.Using the same procedure, 60 g of 2-butyl p-toluenesulfonate and 50 g of tert-butylamine are converted into 7 g of N-tert-butyl-2-butylamine ( b.p. 75O 115 to 117 ° C; hydrochloride mp 173 to 174 ° C).
73 g tert.-Butylamin und 140 g p-Toluolsulfosäure-2-(4-methylpentyl)-ester, der aus 4-Methylpentan-2-ol73 g tert-butylamine and 140 g p-toluenesulfonic acid 2- (4-methylpentyl) ester, that from 4-methylpentan-2-ol
109 749/540109 749/540
und p-Toluolsulfonylchlorid in Pyridin als Öl erhalten wird, erhitzt man 24 Stunden auf 1000C und arbeitet nach der im Beispiel 2 angegebenen Arbeitsweise auf. N-tert.-Butyl-2-(4-methylpentyl)-amin destilliert bei 160 bis 161,5°C. Ausbeute 29,2 g; Hydrochlorid Schmp. 136 bis 1370C.and p-toluenesulfonyl chloride in pyridine is obtained as an oil, it is heated to 100 ° C. for 24 hours and worked up according to the procedure given in Example 2. N-tert-butyl-2- (4-methylpentyl) amine distilled at 160 to 161.5 ° C. Yield 29.2 g; Hydrochloride mp. 136-137 0 C.
53 g tert.-Amylamin werden mit 63 g Isopropylbromid und 50 ecm Glycerin 30 Stunden unter Rückfluß erhitzt. Man destilliert das Reaktionsprodukt an der Widmerkolonne und erhält 30 g N-tert.-Amyl-2-propylamin, Κρ.7β0 125 bis 127°C; Hydrochlorid F. 138°C.53 g of tert-amylamine are refluxed for 30 hours with 63 g of isopropyl bromide and 50 ecm of glycerol. The reaction product is distilled on the Widmer column and 30 g of N-tert-amyl-2-propylamine, Κρ, are obtained. 7β0 125 to 127 ° C; Hydrochloride mp 138 ° C.
In der gleichen Arbeitsweise erhält man aus tert.-Butylamin und sek.-Amylbromid N-tert.-Butylamino-2-pentan, Kp.7B0 138 bis 1400C; Hydrochlorid F. 185 bis 186° C.In the same operation is obtained from tert-butyl and sec-amyl bromide N-tert-butylamino-2-pentane, bp 7B0 138 to 140 0 C. Hydrochloride F. 185 to 186 ° C.
Claims (1)
wobei R Wasserstoff oder eine gerade oder verzweigte Alkylgruppe mit 1 bis 4 Kohlenstoffatomen und R' einen Alkylrest mit 1 bis 3 Kohlenstoffatomen und R" einen gesättigten oder ungesättigten Alkylrest mit 1 bis 3 Kohlenstoffatomen, der durch Hydroxylgruppen substituiert sein kann, bedeutet, dadurch gekennzeichnet, daß man entwederCH 3
where R denotes hydrogen or a straight or branched alkyl group with 1 to 4 carbon atoms and R 'denotes an alkyl group with 1 to 3 carbon atoms and R "denotes a saturated or unsaturated alkyl group with 1 to 3 carbon atoms which can be substituted by hydroxyl groups, characterized in that that one either
R — CH2 — C(CH3)2 — NH2
umsetzt oder daß manwith primary amines of the formula
R - CH 2 - C (CH 3 ) 2 - NH 2
implement or that one
bzw.
R — CH2 — C(CH3)2 — N = CH — R"R - CH 2 - C (CHs) 2 - N = CH - R '
respectively.
R - CH 2 - C (CH 3 ) 2 - N = CH - R "
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28066A DE1119287B (en) | 1959-03-28 | 1959-03-28 | Process for the preparation of blood pressure-effective secondary amines |
| BE589125A BE589125A (en) | 1959-03-28 | 1960-03-28 | Manufacture of secondary amines acting on blood pressure. |
| FR837167A FR456M (en) | 1959-03-28 | 1960-08-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28066A DE1119287B (en) | 1959-03-28 | 1959-03-28 | Process for the preparation of blood pressure-effective secondary amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1119287B true DE1119287B (en) | 1961-12-14 |
Family
ID=7092731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28066A Pending DE1119287B (en) | 1959-03-28 | 1959-03-28 | Process for the preparation of blood pressure-effective secondary amines |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE589125A (en) |
| DE (1) | DE1119287B (en) |
| FR (1) | FR456M (en) |
-
1959
- 1959-03-28 DE DEF28066A patent/DE1119287B/en active Pending
-
1960
- 1960-03-28 BE BE589125A patent/BE589125A/en unknown
- 1960-08-30 FR FR837167A patent/FR456M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BE589125A (en) | 1960-07-18 |
| FR456M (en) | 1961-04-24 |
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