FR2420528A1 - Epimerisation of 3-vinyl-piperidine derivs. - by heating in acid medium above 50 degrees C (DK 15.10.79) - Google Patents
Epimerisation of 3-vinyl-piperidine derivs. - by heating in acid medium above 50 degrees C (DK 15.10.79)Info
- Publication number
- FR2420528A1 FR2420528A1 FR7808449A FR7808449A FR2420528A1 FR 2420528 A1 FR2420528 A1 FR 2420528A1 FR 7808449 A FR7808449 A FR 7808449A FR 7808449 A FR7808449 A FR 7808449A FR 2420528 A1 FR2420528 A1 FR 2420528A1
- Authority
- FR
- France
- Prior art keywords
- vinyl
- epimerisation
- degrees
- heating
- acid medium
- 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.)
- Granted
Links
- LYMGNRHDFKUCDQ-UHFFFAOYSA-N 3-ethenylpiperidine Chemical compound C=CC1CCCNC1 LYMGNRHDFKUCDQ-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title abstract 2
- 238000010438 heat treatment Methods 0.000 title abstract 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract 1
- 229930013930 alkaloid Natural products 0.000 abstract 1
- 150000003797 alkaloid derivatives Chemical class 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- 229940033495 antimalarials Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 229960000948 quinine Drugs 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Process for epimerisation of 3-vinyl-piperidine derives. of formula (I)(where R = H or a substit.) in which the C-atom carrying the vinyl group has configuration R, to give cpds. in which the vinyl-carrying C-atom has configuration S or vice-versa, by heating (I) in acid medium above 50 degrees C and isolating the desired epimer. Used in the synthesis of pharmaceutical intermediates, used to prepare cpds. such as the antiarrhythmics and antimalarials described in FR 2012152 and quinine (cinchora) alkaloid derivs. The epimerisation is pref. effected at 120-160 degrees C in aqueous or aq. alkanoic medium at pH 1-4.
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7808449A FR2420528A1 (en) | 1978-03-23 | 1978-03-23 | Epimerisation of 3-vinyl-piperidine derivs. - by heating in acid medium above 50 degrees C (DK 15.10.79) |
| GR58494A GR69926B (en) | 1978-03-23 | 1979-02-27 | |
| IL56815A IL56815A (en) | 1978-03-23 | 1979-03-07 | Epimerisation of 3-vinylpiperidine derivatives |
| PT69327A PT69327A (en) | 1978-03-23 | 1979-03-09 | PROCESS FOR THE ISOMERISATION OF VINYL-3 PIPERIDINE DERIVATIVES |
| DE7979400167T DE2961396D1 (en) | 1978-03-23 | 1979-03-14 | Process for the isomerization of 3-vinyl-piperidine derivatives |
| EP79400167A EP0005654B1 (en) | 1978-03-23 | 1979-03-14 | Process for the isomerization of 3-vinyl-piperidine derivatives |
| DK111779A DK150616C (en) | 1978-03-23 | 1979-03-19 | PROCEDURE FOR ISOMERIZATION OF DERIVATIVES OF 3-VINYL PIPERIDINE |
| JP3317079A JPS54135775A (en) | 1978-03-23 | 1979-03-20 | Isomerization of 33vinylpiperidine derivative |
| AT0212179A AT370412B (en) | 1978-03-23 | 1979-03-21 | METHOD FOR CONVERTING 3-VINYLPIPERIDINE DERIVATIVES INTO YOUR EPIMERS |
| US06/022,544 US4238612A (en) | 1978-03-23 | 1979-03-21 | Process for the isomerization of derivatives of 3-vinyl-piperidine |
| ES478886A ES478886A1 (en) | 1978-03-23 | 1979-03-22 | Process for the isomerization of 3-vinyl-piperidine derivatives. |
| AU45333/79A AU524171B2 (en) | 1978-03-23 | 1979-03-22 | Isomerisation of derivatives of 3-vinyl-piperidine |
| NO790972A NO153651C (en) | 1978-03-23 | 1979-03-22 | PROCEDURE FOR ISOMERIZATION OF DERIVATIVES OF 3-VINYL PIPERIDINE. |
| AR275909A AR227873A1 (en) | 1978-03-23 | 1979-03-22 | A VINYL-3-PIPERIDINE DERIVATIVES ISOMERIZATION PROCEDURE |
| CA324,087A CA1127647A (en) | 1978-03-23 | 1979-03-22 | Isomerization process of vinyl-3 piperidine derivatives |
| ZA791380A ZA791380B (en) | 1978-03-23 | 1979-03-22 | A process for isomerisation of derivatives of 3-vinyl pipeeridine |
| HU79PA1348A HU181929B (en) | 1978-03-23 | 1979-03-22 | Process for producing 3-vinyl-piperidine derivatives with isomerisation |
| MX10118679U MX5638E (en) | 1978-03-23 | 1979-03-22 | ISOMERIZATION PROCEDURE OF THE VINYL-3 PIPERIDINE DERIVATIVES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7808449A FR2420528A1 (en) | 1978-03-23 | 1978-03-23 | Epimerisation of 3-vinyl-piperidine derivs. - by heating in acid medium above 50 degrees C (DK 15.10.79) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2420528A1 true FR2420528A1 (en) | 1979-10-19 |
| FR2420528B1 FR2420528B1 (en) | 1980-08-29 |
Family
ID=9206200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7808449A Granted FR2420528A1 (en) | 1978-03-23 | 1978-03-23 | Epimerisation of 3-vinyl-piperidine derivs. - by heating in acid medium above 50 degrees C (DK 15.10.79) |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2420528A1 (en) |
| ZA (1) | ZA791380B (en) |
-
1978
- 1978-03-23 FR FR7808449A patent/FR2420528A1/en active Granted
-
1979
- 1979-03-22 ZA ZA791380A patent/ZA791380B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2420528B1 (en) | 1980-08-29 |
| ZA791380B (en) | 1980-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |