IL29781A - Process for the preparation of the optical isomers of 1-ethyl-2-aminomethyl-pyrrolidine - Google Patents
Process for the preparation of the optical isomers of 1-ethyl-2-aminomethyl-pyrrolidineInfo
- Publication number
- IL29781A IL29781A IL29781A IL2978168A IL29781A IL 29781 A IL29781 A IL 29781A IL 29781 A IL29781 A IL 29781A IL 2978168 A IL2978168 A IL 2978168A IL 29781 A IL29781 A IL 29781A
- Authority
- IL
- Israel
- Prior art keywords
- preparation
- pure
- purified
- base
- crude
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000003287 optical effect Effects 0.000 title description 6
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical class CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 239000002585 base Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR104008A FR1528014A (fr) | 1967-04-24 | 1967-04-24 | Procédé de préparation des isomères optiques de la éthyl-1, aminométhyl-2-pyrrolidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL29781A0 IL29781A0 (en) | 1968-06-20 |
| IL29781A true IL29781A (en) | 1971-08-25 |
Family
ID=8629548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL29781A IL29781A (en) | 1967-04-24 | 1968-04-08 | Process for the preparation of the optical isomers of 1-ethyl-2-aminomethyl-pyrrolidine |
Country Status (19)
| Country | Link |
|---|---|
| AT (1) | AT278771B (OSRAM) |
| BE (1) | BE712925A (OSRAM) |
| BR (1) | BR6898525D0 (OSRAM) |
| CH (1) | CH484899A (OSRAM) |
| CS (1) | CS153010B2 (OSRAM) |
| DE (1) | DE1795712A1 (OSRAM) |
| DK (1) | DK129285B (OSRAM) |
| ES (1) | ES352901A1 (OSRAM) |
| FR (1) | FR1528014A (OSRAM) |
| GB (1) | GB1207752A (OSRAM) |
| IE (1) | IE32006B1 (OSRAM) |
| IL (1) | IL29781A (OSRAM) |
| IT (1) | IT954025B (OSRAM) |
| MC (1) | MC715A1 (OSRAM) |
| NL (1) | NL6805746A (OSRAM) |
| OA (1) | OA02787A (OSRAM) |
| PL (1) | PL72570B1 (OSRAM) |
| SE (1) | SE323375B (OSRAM) |
| YU (1) | YU32376B (OSRAM) |
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 (sv) * | 1982-09-30 | 1987-01-12 | Astra Pharma Prod | Diastereomerer av di-p-toluoyltartrat med 1-etyl-2-aminometylpyrrolidin och forfarande for framstellning av dessa |
| DE4425070A1 (de) * | 1994-07-15 | 1996-01-18 | Degussa | Verfahren zur Herstellung optisch aktiver l-substituierter 2-(Aminomethyl)pyrrolidine |
-
1967
- 1967-04-24 FR FR104008A patent/FR1528014A/fr not_active Expired
-
1968
- 1968-03-29 BE BE712925D patent/BE712925A/xx not_active IP Right Cessation
- 1968-04-02 MC MC754A patent/MC715A1/fr unknown
- 1968-04-03 OA OA53237A patent/OA02787A/xx unknown
- 1968-04-05 IE IE395/68A patent/IE32006B1/xx unknown
- 1968-04-08 IL IL29781A patent/IL29781A/en unknown
- 1968-04-08 DE DE19681795712 patent/DE1795712A1/de active Pending
- 1968-04-19 ES ES352901A patent/ES352901A1/es not_active Expired
- 1968-04-19 YU YU0939/68A patent/YU32376B/xx unknown
- 1968-04-20 IT IT36469/68A patent/IT954025B/it active
- 1968-04-22 GB GB08932/68A patent/GB1207752A/en not_active Expired
- 1968-04-23 PL PL1968126595A patent/PL72570B1/pl unknown
- 1968-04-23 NL NL6805746A patent/NL6805746A/xx unknown
- 1968-04-23 DK DK181368AA patent/DK129285B/da unknown
- 1968-04-23 CH CH596068A patent/CH484899A/fr not_active IP Right Cessation
- 1968-04-23 BR BR198525/68A patent/BR6898525D0/pt unknown
- 1968-04-23 SE SE5404/68A patent/SE323375B/xx unknown
- 1968-04-24 CS CS303668A patent/CS153010B2/cs unknown
- 1968-04-24 AT AT400868A patent/AT278771B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU93968A (en) | 1974-04-30 |
| DE1795712A1 (de) | 1973-10-18 |
| BE712925A (OSRAM) | 1968-09-30 |
| CH484899A (fr) | 1970-01-31 |
| FR1528014A (fr) | 1968-06-07 |
| IE32006L (en) | 1968-10-24 |
| IL29781A0 (en) | 1968-06-20 |
| DK129285B (da) | 1974-09-23 |
| DK129285C (OSRAM) | 1975-02-10 |
| GB1207752A (en) | 1970-10-07 |
| SE323375B (OSRAM) | 1970-05-04 |
| OA02787A (fr) | 1970-12-15 |
| IE32006B1 (en) | 1973-03-07 |
| NL6805746A (OSRAM) | 1968-10-25 |
| CS153010B2 (OSRAM) | 1974-02-22 |
| AT278771B (de) | 1970-02-10 |
| MC715A1 (fr) | 1969-02-05 |
| PL72570B1 (OSRAM) | 1974-08-30 |
| YU32376B (en) | 1974-10-31 |
| IT954025B (it) | 1973-08-30 |
| BR6898525D0 (pt) | 1973-05-10 |
| ES352901A1 (es) | 1969-09-01 |
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