PL72570B1 - - Google Patents
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- Publication number
- PL72570B1 PL72570B1 PL1968126595A PL12659568A PL72570B1 PL 72570 B1 PL72570 B1 PL 72570B1 PL 1968126595 A PL1968126595 A PL 1968126595A PL 12659568 A PL12659568 A PL 12659568A PL 72570 B1 PL72570 B1 PL 72570B1
- Authority
- PL
- Poland
- Prior art keywords
- tartrate
- tartaric acid
- ethyl
- aminomethylpyrrolidine
- handed
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 16
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical class CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 14
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 13
- 229940095064 tartrate Drugs 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- -1 d-tartrate amine Chemical class 0.000 claims description 8
- 229960001367 tartaric acid Drugs 0.000 claims description 8
- 239000011975 tartaric acid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229960001270 d- tartaric acid Drugs 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003892 tartrate salts Chemical class 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 229940054066 benzamide antipsychotics Drugs 0.000 description 4
- 150000003936 benzamides Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000013078 crystal Substances 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 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 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 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 (1)
| Publication Number | Publication Date |
|---|---|
| PL72570B1 true PL72570B1 (OSRAM) | 1974-08-30 |
Family
ID=8629548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1968126595A PL72570B1 (OSRAM) | 1967-04-24 | 1968-04-23 |
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 |
| IL29781A (en) | 1971-08-25 |
| YU32376B (en) | 1974-10-31 |
| IT954025B (it) | 1973-08-30 |
| BR6898525D0 (pt) | 1973-05-10 |
| ES352901A1 (es) | 1969-09-01 |
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