FI56376C - Foerfarande foer framstaellning av 1-alkenyl-2-aminometylpyrrolidiner - Google Patents
Foerfarande foer framstaellning av 1-alkenyl-2-aminometylpyrrolidiner Download PDFInfo
- Publication number
- FI56376C FI56376C FI1974/72A FI197472A FI56376C FI 56376 C FI56376 C FI 56376C FI 1974/72 A FI1974/72 A FI 1974/72A FI 197472 A FI197472 A FI 197472A FI 56376 C FI56376 C FI 56376C
- Authority
- FI
- Finland
- Prior art keywords
- allyl
- added
- alkenyl
- temperature
- pyrrolidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- HTGKTSVPJJNEMQ-QMMMGPOBSA-N [(2s)-1-prop-2-enylpyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC=C HTGKTSVPJJNEMQ-QMMMGPOBSA-N 0.000 claims 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
-
- 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
- C07D207/22—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 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1434171 | 1971-09-30 | ||
| CH1434171A CH556836A (de) | 1971-09-30 | 1971-09-30 | Verfahren zur herstellung von 1-alkenyl-2-aminomethylpyrrolidinen. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56376B FI56376B (fi) | 1979-09-28 |
| FI56376C true FI56376C (fi) | 1980-01-10 |
Family
ID=4399993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1974/72A FI56376C (fi) | 1971-09-30 | 1972-07-11 | Foerfarande foer framstaellning av 1-alkenyl-2-aminometylpyrrolidiner |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3849442A (en:Method) |
| JP (1) | JPS552426B2 (en:Method) |
| KR (1) | KR780000047B1 (en:Method) |
| AT (1) | AT314529B (en:Method) |
| AU (1) | AU464364B2 (en:Method) |
| BE (1) | BE785907A (en:Method) |
| BG (1) | BG19149A3 (en:Method) |
| CA (1) | CA959852A (en:Method) |
| CH (1) | CH556836A (en:Method) |
| CS (1) | CS166660B2 (en:Method) |
| DD (1) | DD97885A5 (en:Method) |
| DE (1) | DE2216738C3 (en:Method) |
| EG (1) | EG10787A (en:Method) |
| ES (1) | ES401286A1 (en:Method) |
| FI (1) | FI56376C (en:Method) |
| FR (1) | FR2154423B1 (en:Method) |
| GB (1) | GB1346859A (en:Method) |
| HU (1) | HU163531B (en:Method) |
| IE (1) | IE36428B1 (en:Method) |
| IL (1) | IL39668A (en:Method) |
| IT (1) | IT1037039B (en:Method) |
| LU (1) | LU65690A1 (en:Method) |
| MC (1) | MC931A1 (en:Method) |
| NL (1) | NL7206705A (en:Method) |
| OA (1) | OA04150A (en:Method) |
| PH (1) | PH11770A (en:Method) |
| PL (1) | PL82315B1 (en:Method) |
| RO (1) | RO59001A (en:Method) |
| SE (1) | SE383341B (en:Method) |
| YU (1) | YU34618B (en:Method) |
| ZM (1) | ZM9472A1 (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH602636A5 (en:Method) * | 1974-03-04 | 1978-07-31 | Ile De France |
-
1971
- 1971-09-30 CH CH1434171A patent/CH556836A/xx not_active IP Right Cessation
-
1972
- 1972-03-11 RO RO70077A patent/RO59001A/ro unknown
- 1972-03-21 HU HUFA906A patent/HU163531B/hu unknown
- 1972-03-24 BG BG020054A patent/BG19149A3/xx unknown
- 1972-03-28 ES ES401286A patent/ES401286A1/es not_active Expired
- 1972-03-28 IT IT22492/72A patent/IT1037039B/it active
- 1972-04-07 DE DE2216738A patent/DE2216738C3/de not_active Expired
- 1972-04-13 YU YU990/72A patent/YU34618B/xx unknown
- 1972-04-28 SE SE7205646A patent/SE383341B/xx unknown
- 1972-05-05 PL PL1972155185A patent/PL82315B1/pl unknown
- 1972-05-10 CA CA141,818A patent/CA959852A/en not_active Expired
- 1972-05-11 GB GB2203772A patent/GB1346859A/en not_active Expired
- 1972-05-11 DD DD162968A patent/DD97885A5/xx unknown
- 1972-05-17 NL NL7206705A patent/NL7206705A/xx unknown
- 1972-05-17 US US00254235A patent/US3849442A/en not_active Expired - Lifetime
- 1972-05-18 AU AU42457/72A patent/AU464364B2/en not_active Expired
- 1972-06-06 ZM ZM94/72*UA patent/ZM9472A1/xx unknown
- 1972-06-12 IL IL39668A patent/IL39668A/xx unknown
- 1972-06-16 KR KR7200941A patent/KR780000047B1/ko not_active Expired
- 1972-06-20 AT AT530272A patent/AT314529B/de not_active IP Right Cessation
- 1972-06-20 IE IE864/72A patent/IE36428B1/xx unknown
- 1972-06-20 MC MC998A patent/MC931A1/xx unknown
- 1972-07-04 FR FR7224161A patent/FR2154423B1/fr not_active Expired
- 1972-07-06 BE BE785907A patent/BE785907A/xx not_active IP Right Cessation
- 1972-07-07 LU LU65690A patent/LU65690A1/xx unknown
- 1972-07-11 FI FI1974/72A patent/FI56376C/fi active
- 1972-08-09 OA OA54658A patent/OA04150A/xx unknown
- 1972-09-13 CS CS6273*BA patent/CS166660B2/cs unknown
- 1972-09-25 PH PH13936A patent/PH11770A/en unknown
- 1972-09-28 EG EG394/72A patent/EG10787A/xx active
- 1972-09-30 JP JP9856372A patent/JPS552426B2/ja not_active Expired
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