IE35775L - 1 - alkyl - 2 - aminoethylpyrrolidines - Google Patents
1 - alkyl - 2 - aminoethylpyrrolidinesInfo
- Publication number
- IE35775L IE35775L IE711354A IE135471A IE35775L IE 35775 L IE35775 L IE 35775L IE 711354 A IE711354 A IE 711354A IE 135471 A IE135471 A IE 135471A IE 35775 L IE35775 L IE 35775L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- acid
- pyrrolidine
- solvent
- group
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 abstract 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-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
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- -1 nitromethylene group Chemical group 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- C07D207/10—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)
- Catalysts (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 -20‹C. 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.
[GB1374818A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE35775L true IE35775L (en) | 1972-05-10 |
| IE35775B1 IE35775B1 (en) | 1976-05-12 |
Family
ID=4418871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1354/71A IE35775B1 (en) | 1970-11-10 | 1971-10-26 | Preparation of 1-alkyl-2-aminomethylpyrrolidines |
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 ES ES396293A patent/ES396293A1/en not_active Expired
- 1971-10-22 IL IL37994A patent/IL37994A/en unknown
- 1971-10-26 MC MC953A patent/MC896A1/en unknown
- 1971-10-26 CA CA126,128A patent/CA940533A/en not_active Expired
- 1971-10-26 BG BG018861A patent/BG21605A3/en unknown
- 1971-10-26 IE IE1354/71A patent/IE35775B1/en unknown
- 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 GB GB5122571A patent/GB1374818A/en not_active Expired
- 1971-11-04 CS CS7100007753A patent/CS186206B2/en unknown
- 1971-11-05 OA OA54406A patent/OA03823A/en unknown
- 1971-11-08 PL PL1971151433A patent/PL81412B1/pl unknown
- 1971-11-08 FI FI3193/71A patent/FI54471C/en active
- 1971-11-08 LU LU64227D patent/LU64227A1/xx unknown
- 1971-11-09 HU HUFA897A patent/HU162787B/hu unknown
- 1971-11-09 YU YU2823/71A patent/YU34672B/en unknown
- 1971-11-09 SE SE7114274A patent/SE376415B/xx unknown
- 1971-11-09 DK DK548871A patent/DK145573C/en not_active IP Right Cessation
- 1971-11-10 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 |
|---|---|
| FI54471C (en) | 1978-12-11 |
| IT1043845B (en) | 1980-02-29 |
| IL37994A (en) | 1974-10-22 |
| LU64227A1 (en) | 1972-05-29 |
| DK145573B (en) | 1982-12-13 |
| FR2111371A5 (en) | 1972-06-02 |
| AU464960B2 (en) | 1975-09-11 |
| AT311952B (en) | 1973-12-10 |
| IE35775B1 (en) | 1976-05-12 |
| NL7114901A (en) | 1972-05-15 |
| CA940533A (en) | 1974-01-22 |
| YU34672B (en) | 1979-12-31 |
| SE376415B (en) | 1975-05-26 |
| CH532035A (en) | 1972-12-31 |
| DK145573C (en) | 1983-05-30 |
| HU162787B (en) | 1973-04-28 |
| BG21605A3 (en) | 1976-07-20 |
| DE2152371A1 (en) | 1972-06-22 |
| YU282371A (en) | 1979-07-10 |
| MC896A1 (en) | 1972-06-22 |
| PH12022A (en) | 1978-10-06 |
| BE773979A (en) | 1972-04-17 |
| PL81412B1 (en) | 1975-08-30 |
| CS186206B2 (en) | 1978-11-30 |
| ES396293A1 (en) | 1974-05-01 |
| AU3479071A (en) | 1973-05-03 |
| GB1374818A (en) | 1974-11-20 |
| FI54471B (en) | 1978-08-31 |
| IL37994A0 (en) | 1971-12-29 |
| OA03823A (en) | 1971-12-24 |
| ZM15171A1 (en) | 1972-07-21 |
| ZA716998B (en) | 1972-07-26 |
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