GB1374818A - Preparation of 1-alkyl-2-aminomethyl-pyrrolidines - Google Patents
Preparation of 1-alkyl-2-aminomethyl-pyrrolidinesInfo
- Publication number
- GB1374818A GB1374818A GB5122571A GB5122571A GB1374818A GB 1374818 A GB1374818 A GB 1374818A GB 5122571 A GB5122571 A GB 5122571A GB 5122571 A GB5122571 A GB 5122571A GB 1374818 A GB1374818 A GB 1374818A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- acid
- pyrrolidine
- solvent
- group
- 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
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
- C07D207/10—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- 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
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
1374818 1 - Alkyl - 2 - aminomethylpyrrolidines FRATMANN SA 4 Nov 1971 [10 Nov 1970] 51225/71 Heading C2C 1 - Alkyl - 2 - aminomethylpyrrolidines are prepared by reacting a 1-alkyl-2-pyrrolidine in a solvent, e.g. benzene, toluene or xylene, with phosgene at - 5 to + 10 C.; reacting the resultant product, optionally after isolation and purification of the same, with an alkali metal alcoholate at 0 to -20C. and then with nitromethane at room temperature; and finally reducing the resultant nitromethylene group to an aminoethyl group. The 1-alkyl-2-nitromethylenepyrrolidine may also be isolated and purified before the reduction and the latter is preferably carried out (i) by catalytic hydrogenation in an inert solvent, e.g. Pt black, Rh on Al 2 O 3 , Pd on charcoal and Raney Ni in water, methanol, ethanol, isopropanol, butanol, tetrahydrofuran or dioxane or (ii) by hydrogen produced in situ by the reaction of an acid on a metal. In the first step of the process the phosgene may be first dissolved in the solvent and then the solution formed added to the 1- alkyl - 2 - pyrrolidine. The 1 - alkyl - 2- aminomethyl pyrrolidine may be converted to a salt by the addition of an acid, e.g. HCl, HBr, H 2 SO 4 , oxalic acid, tartaric acid, maleic acid or picric acid. Examples of the alkyl group in the product are methyl, ethyl (see example), propyl, isopropyl and isobutyl groups. Reference has been directed by the Comptroller to Specification 1,236,842.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1662870A CH532035A (en) | 1970-11-10 | 1970-11-10 | New process for the preparation of 1-alkyl-2-amino-methylpyrrolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1374818A true GB1374818A (en) | 1974-11-20 |
Family
ID=4418871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5122571A Expired GB1374818A (en) | 1970-11-10 | 1971-11-04 | Preparation of 1-alkyl-2-aminomethyl-pyrrolidines |
Country Status (27)
| Country | Link |
|---|---|
| AT (1) | AT311952B (en) |
| AU (1) | AU464960B2 (en) |
| BE (1) | BE773979A (en) |
| BG (1) | BG21605A3 (en) |
| CA (1) | CA940533A (en) |
| CH (1) | CH532035A (en) |
| CS (1) | CS186206B2 (en) |
| DE (1) | DE2152371A1 (en) |
| DK (1) | DK145573C (en) |
| ES (1) | ES396293A1 (en) |
| FI (1) | FI54471C (en) |
| FR (1) | FR2111371A5 (en) |
| GB (1) | GB1374818A (en) |
| HU (1) | HU162787B (en) |
| IE (1) | IE35775B1 (en) |
| IL (1) | IL37994A (en) |
| IT (1) | IT1043845B (en) |
| LU (1) | LU64227A1 (en) |
| MC (1) | MC896A1 (en) |
| NL (1) | NL7114901A (en) |
| OA (1) | OA03823A (en) |
| PH (1) | PH12022A (en) |
| PL (1) | PL81412B1 (en) |
| SE (1) | SE376415B (en) |
| YU (1) | YU34672B (en) |
| ZA (1) | ZA716998B (en) |
| ZM (1) | ZM15171A1 (en) |
-
1970
- 1970-11-10 CH CH1662870A patent/CH532035A/en not_active IP Right Cessation
-
1971
- 1971-10-14 FR FR7136940A patent/FR2111371A5/fr not_active Expired
- 1971-10-15 BE BE773979A patent/BE773979A/en not_active IP Right Cessation
- 1971-10-19 ZA ZA716998A patent/ZA716998B/en unknown
- 1971-10-20 AU AU34790/71A patent/AU464960B2/en not_active Expired
- 1971-10-21 DE DE19712152371 patent/DE2152371A1/en active Pending
- 1971-10-22 IL IL37994A patent/IL37994A/en unknown
- 1971-10-22 ES ES396293A patent/ES396293A1/en not_active Expired
- 1971-10-26 IE IE1354/71A patent/IE35775B1/en unknown
- 1971-10-26 BG BG18861A patent/BG21605A3/xx unknown
- 1971-10-26 MC MC953A patent/MC896A1/en unknown
- 1971-10-26 CA CA126,128A patent/CA940533A/en not_active Expired
- 1971-10-27 ZM ZM151/71A patent/ZM15171A1/en unknown
- 1971-10-28 NL NL7114901A patent/NL7114901A/xx unknown
- 1971-10-29 IT IT30520/71A patent/IT1043845B/en active
- 1971-11-04 CS CS7100007753A patent/CS186206B2/en unknown
- 1971-11-04 GB GB5122571A patent/GB1374818A/en not_active Expired
- 1971-11-05 OA OA54406A patent/OA03823A/en unknown
- 1971-11-08 FI FI3193/71A patent/FI54471C/en active
- 1971-11-08 PL PL1971151433A patent/PL81412B1/pl unknown
- 1971-11-08 LU LU64227D patent/LU64227A1/xx unknown
- 1971-11-09 HU HUFA897A patent/HU162787B/hu unknown
- 1971-11-09 SE SE7114274A patent/SE376415B/xx unknown
- 1971-11-09 DK DK548871A patent/DK145573C/en not_active IP Right Cessation
- 1971-11-09 YU YU2823/71A patent/YU34672B/en unknown
- 1971-11-10 AT AT969071A patent/AT311952B/en not_active IP Right Cessation
- 1971-11-10 PH PH13000A patent/PH12022A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES396293A1 (en) | 1974-05-01 |
| AT311952B (en) | 1973-12-10 |
| IE35775B1 (en) | 1976-05-12 |
| SE376415B (en) | 1975-05-26 |
| YU34672B (en) | 1979-12-31 |
| CA940533A (en) | 1974-01-22 |
| AU464960B2 (en) | 1975-09-11 |
| CS186206B2 (en) | 1978-11-30 |
| PH12022A (en) | 1978-10-06 |
| BE773979A (en) | 1972-04-17 |
| PL81412B1 (en) | 1975-08-30 |
| FR2111371A5 (en) | 1972-06-02 |
| OA03823A (en) | 1971-12-24 |
| ZM15171A1 (en) | 1972-07-21 |
| FI54471C (en) | 1978-12-11 |
| DE2152371A1 (en) | 1972-06-22 |
| ZA716998B (en) | 1972-07-26 |
| BG21605A3 (en) | 1976-07-20 |
| LU64227A1 (en) | 1972-05-29 |
| NL7114901A (en) | 1972-05-15 |
| HU162787B (en) | 1973-04-28 |
| DK145573C (en) | 1983-05-30 |
| IE35775L (en) | 1972-05-10 |
| FI54471B (en) | 1978-08-31 |
| AU3479071A (en) | 1973-05-03 |
| YU282371A (en) | 1979-07-10 |
| DK145573B (en) | 1982-12-13 |
| CH532035A (en) | 1972-12-31 |
| IT1043845B (en) | 1980-02-29 |
| MC896A1 (en) | 1972-06-22 |
| IL37994A0 (en) | 1971-12-29 |
| IL37994A (en) | 1974-10-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1277624C (en) | Process for preparing 1-deoxynojirimycin and n-derivatives thereof | |
| Leeds et al. | A Mild Single-Step Reduction of Oximes to Amines1 | |
| Evans | The Structure of Alkyl-Substituted Pyrrolines1 | |
| GB1341423A (en) | Process for the production of cyclopentene from cyclopentadiene | |
| Saito et al. | Structures of norsecurinine and dihydronorsecurinine | |
| NO146198B (en) | INTERMEDIATE FOR PREPARATION OF 5-FLUORO-2-METHYL-1- (P-METHYLSULPHINYLBENZYLIDE) -IND-2-EN-3-YL-ACETIC ACID | |
| GB1374818A (en) | Preparation of 1-alkyl-2-aminomethyl-pyrrolidines | |
| McKennis Jr et al. | Metabolites of nicotine and a synthesis of nornicotine | |
| EP0162444B1 (en) | Process for preparing rimantadine | |
| US3780019A (en) | Production of erythromycylamine compounds | |
| US4115387A (en) | 3-Methyl-4-phenyl-1,2,3,4-tetrahydrobenz [H]isoquinoline hydrobromide | |
| US2838526A (en) | Hydrogenation of steroid compounds | |
| US3330835A (en) | Novel 1, 3, 4, 5-tetrahydropyrrolo [4, 3, 2-de] quinolines | |
| US3467710A (en) | Beta-(4- or 5-phenyl-1-naphthalene) ethylamines | |
| US3748333A (en) | Palladium hydrogenation process for 3,4 dihydroisoquinalines | |
| Yamada et al. | Reduction of acid amides to amines with sodium borohydride | |
| US2970159A (en) | Hydrazine derivatives | |
| US2801249A (en) | Process for producing alpha-phenyl succinimides | |
| US3413293A (en) | Method for producing 2, 3, 4, 6, 7, 12-hexahydroindolo-[2, 3-a] quinolizine | |
| US3629272A (en) | Process for producing 6-halo-4-azabenzimidazoles and intermediates therefor | |
| Abramovitch | TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS: PART IV. ATTEMPTED SYNTHESIS OF THE PHYSOSTIGMINE RING SYSTEM | |
| US3381014A (en) | Process for producing pyridoxine and novel intermediates thereof | |
| US3187051A (en) | Process for the preparation of unsymmetrical dialkyl hydrazines | |
| US3207749A (en) | Process for the production of dihydro glucosides | |
| YATSUNAMI et al. | Chemical Conversion of Kobusine: Cleavage of the Bridged CC Bond by a Novel Fragmentation Reaction |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |