ES352901A1 - Process for the preparation of the optical isomers of 1-ethyl -2-aminoethylpyrrolidine - Google Patents
Process for the preparation of the optical isomers of 1-ethyl -2-aminoethylpyrrolidineInfo
- Publication number
- ES352901A1 ES352901A1 ES352901A ES352901A ES352901A1 ES 352901 A1 ES352901 A1 ES 352901A1 ES 352901 A ES352901 A ES 352901A ES 352901 A ES352901 A ES 352901A ES 352901 A1 ES352901 A1 ES 352901A1
- Authority
- ES
- Spain
- Prior art keywords
- ethyl
- tartrate
- pyrrolidine
- aminomethyl
- optically active
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 3
- WMFCMIRCRKQLRO-UHFFFAOYSA-N 2-pyrrolidin-1-ylbutan-1-amine Chemical class CCC(CN)N1CCCC1 WMFCMIRCRKQLRO-UHFFFAOYSA-N 0.000 title 1
- 230000003287 optical effect Effects 0.000 title 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical class CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- 150000003892 tartrate salts Chemical class 0.000 abstract 2
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 229960001270 d- tartaric acid Drugs 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960001367 tartaric acid Drugs 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The levorotatory and dextrorotatory isomers of 1 - ethyl - 2 - aminomethyl - pyrrolidine are separated by a process comprising forming a tartrate salt of a mixture of said isomers with an optically active tartaric acid and separating an optically active tartrate salt by crystallization. It is preferred to treat the pyrrolidine first with d - tartaric acid which leads to crystallization of the d-tartrate of dextrorotatory 1 - ethyl - 2 - aminomethyl - pyrrolidine. The crystals are removed by filtration and the optically active amine may be liberated conventionally from the tartrate. The filtrate is then rendered alkaline and treated with I - tartaric acid to yield the l - tartrate of l - 1 - amino - 2 - aminomethyl - pyrrolidine in the crystalline state. If desired, the method of treatment may be reversed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR104008A FR1528014A (en) | 1967-04-24 | 1967-04-24 | Process for the preparation of optical isomers of ethyl-1, aminomethyl-2-pyrrolidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES352901A1 true ES352901A1 (en) | 1969-09-01 |
Family
ID=8629548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES352901A Expired ES352901A1 (en) | 1967-04-24 | 1968-04-19 | Process for the preparation of the optical isomers of 1-ethyl -2-aminoethylpyrrolidine |
Country Status (19)
| Country | Link |
|---|---|
| AT (1) | AT278771B (en) |
| BE (1) | BE712925A (en) |
| BR (1) | BR6898525D0 (en) |
| CH (1) | CH484899A (en) |
| CS (1) | CS153010B2 (en) |
| DE (1) | DE1795712A1 (en) |
| DK (1) | DK129285B (en) |
| ES (1) | ES352901A1 (en) |
| FR (1) | FR1528014A (en) |
| GB (1) | GB1207752A (en) |
| IE (1) | IE32006B1 (en) |
| IL (1) | IL29781A (en) |
| IT (1) | IT954025B (en) |
| MC (1) | MC715A1 (en) |
| NL (1) | NL6805746A (en) |
| OA (1) | OA02787A (en) |
| PL (1) | PL72570B1 (en) |
| SE (1) | SE323375B (en) |
| YU (1) | YU32376B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL52645A (en) * | 1976-08-05 | 1980-02-29 | Synthelabo | Optically active 1 substituted 2 aminomethyl pyrrolidines stereospecifics synthesis thereof and process for the preparation of optically active 2 methoxy n pyrrolidylmethyl benzamides |
| SE447991B (en) * | 1982-09-30 | 1987-01-12 | Astra Pharma Prod | DIASTEREOMERS OF DI-P-TOLUOYL TARTRATE WITH 1-ETHYL-2-AMINOMETHYLPYRROLIDINE AND PROCEDURE FOR PREPARING THESE |
| DE4425070A1 (en) * | 1994-07-15 | 1996-01-18 | Degussa | Process for the preparation of optically active l-substituted 2- (aminomethyl) pyrrolidines |
-
1967
- 1967-04-24 FR FR104008A patent/FR1528014A/en not_active Expired
-
1968
- 1968-03-29 BE BE712925D patent/BE712925A/xx not_active IP Right Cessation
- 1968-04-02 MC MC754A patent/MC715A1/en unknown
- 1968-04-03 OA OA53237A patent/OA02787A/en unknown
- 1968-04-05 IE IE395/68A patent/IE32006B1/en unknown
- 1968-04-08 DE DE19681795712 patent/DE1795712A1/en active Pending
- 1968-04-08 IL IL29781A patent/IL29781A/en unknown
- 1968-04-19 ES ES352901A patent/ES352901A1/en not_active Expired
- 1968-04-19 YU YU0939/68A patent/YU32376B/en unknown
- 1968-04-20 IT IT36469/68A patent/IT954025B/en active
- 1968-04-22 GB GB08932/68A patent/GB1207752A/en not_active Expired
- 1968-04-23 SE SE5404/68A patent/SE323375B/xx unknown
- 1968-04-23 NL NL6805746A patent/NL6805746A/xx unknown
- 1968-04-23 BR BR198525/68A patent/BR6898525D0/en unknown
- 1968-04-23 CH CH596068A patent/CH484899A/en not_active IP Right Cessation
- 1968-04-23 DK DK181368AA patent/DK129285B/en unknown
- 1968-04-23 PL PL1968126595A patent/PL72570B1/pl unknown
- 1968-04-24 AT AT400868A patent/AT278771B/en not_active IP Right Cessation
- 1968-04-24 CS CS303668A patent/CS153010B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE32006L (en) | 1968-10-24 |
| OA02787A (en) | 1970-12-15 |
| YU93968A (en) | 1974-04-30 |
| FR1528014A (en) | 1968-06-07 |
| IL29781A (en) | 1971-08-25 |
| DK129285C (en) | 1975-02-10 |
| PL72570B1 (en) | 1974-08-30 |
| CS153010B2 (en) | 1974-02-22 |
| IL29781A0 (en) | 1968-06-20 |
| IT954025B (en) | 1973-08-30 |
| NL6805746A (en) | 1968-10-25 |
| SE323375B (en) | 1970-05-04 |
| IE32006B1 (en) | 1973-03-07 |
| BE712925A (en) | 1968-09-30 |
| AT278771B (en) | 1970-02-10 |
| DE1795712A1 (en) | 1973-10-18 |
| DK129285B (en) | 1974-09-23 |
| MC715A1 (en) | 1969-02-05 |
| GB1207752A (en) | 1970-10-07 |
| CH484899A (en) | 1970-01-31 |
| BR6898525D0 (en) | 1973-05-10 |
| YU32376B (en) | 1974-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19861127 |