CH624671A5 - Process for the preparation of 2-oxopyrrolidine-N-alkylamides - Google Patents
Process for the preparation of 2-oxopyrrolidine-N-alkylamides Download PDFInfo
- Publication number
- CH624671A5 CH624671A5 CH1643376A CH1643376A CH624671A5 CH 624671 A5 CH624671 A5 CH 624671A5 CH 1643376 A CH1643376 A CH 1643376A CH 1643376 A CH1643376 A CH 1643376A CH 624671 A5 CH624671 A5 CH 624671A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alkylamides
- pyrrolidine
- oxopyrrolidine
- oxo
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 10
- RFIZPYFNEYSHKG-UHFFFAOYSA-N pyrrolidine-2,5-dione;sodium Chemical compound [Na].O=C1CCC(=O)N1 RFIZPYFNEYSHKG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000047 product Substances 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000001704 evaporation Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 5
- 229960002317 succinimide Drugs 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- DQAKJEWZWDQURW-UHFFFAOYSA-N pyrrolidonecarboxylic acid Chemical class OC(=O)N1CCCC1=O DQAKJEWZWDQURW-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000008151 electrolyte solution Substances 0.000 claims description 3
- QAZCPUUJMFBNJO-UHFFFAOYSA-N pyrrolidin-2-one;sodium Chemical compound [Na].O=C1CCCN1 QAZCPUUJMFBNJO-UHFFFAOYSA-N 0.000 claims description 3
- -1 Ethanol Chemical compound 0.000 claims description 2
- 206010020651 Hyperkinesia Diseases 0.000 claims description 2
- 208000000269 Hyperkinesis Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000019430 Motor disease Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical group 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229960004526 piracetam Drugs 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- DBIVLAVBOICUQX-UHFFFAOYSA-N 3-bromopropanamide Chemical compound NC(=O)CCBr DBIVLAVBOICUQX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate 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
- C07D207/18—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
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU78/76A YU39341B (en) | 1976-01-14 | 1976-01-14 | Process for obtaining n-alkylamide-2-oxopyrrolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624671A5 true CH624671A5 (en) | 1981-08-14 |
Family
ID=25548234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1643376A CH624671A5 (en) | 1976-01-14 | 1976-12-29 | Process for the preparation of 2-oxopyrrolidine-N-alkylamides |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS52116463A (cs) |
| AT (1) | AT355013B (cs) |
| CH (1) | CH624671A5 (cs) |
| CS (1) | CS208719B2 (cs) |
| FI (1) | FI63750C (cs) |
| HU (1) | HU172999B (cs) |
| PL (1) | PL103074B1 (cs) |
| SE (1) | SE416730B (cs) |
| SU (1) | SU893131A3 (cs) |
| YU (1) | YU39341B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5933068A (ja) * | 1982-08-17 | 1984-02-22 | Nitsukuu Kogyo Kk | 真空含浸法 |
| JPS59152030A (ja) * | 1983-02-15 | 1984-08-30 | Taiho Kogyo Co Ltd | ダイカスト部品への含浸方法及び装置 |
| JPS59150655A (ja) * | 1983-04-14 | 1984-08-28 | Taiho Kogyo Co Ltd | ダイカスト部品への含浸方法及び装置 |
| JPS62218028A (ja) * | 1986-03-20 | 1987-09-25 | Toyota Motor Corp | 含浸処理方法 |
| RU2629117C1 (ru) * | 2016-06-14 | 2017-08-24 | Сизов Владимир Владимирович | Способ получения 4-замещенного 2-[2-оксо-1-пирролидинил] ацетамида |
-
1976
- 1976-01-14 YU YU78/76A patent/YU39341B/xx unknown
- 1976-12-29 CH CH1643376A patent/CH624671A5/de not_active IP Right Cessation
- 1976-12-30 AT AT980876A patent/AT355013B/de not_active IP Right Cessation
-
1977
- 1977-01-04 CS CS7761A patent/CS208719B2/cs unknown
- 1977-01-10 SE SE7700172A patent/SE416730B/xx not_active IP Right Cessation
- 1977-01-11 HU HU77PI00000559A patent/HU172999B/hu unknown
- 1977-01-12 SU SU772439826A patent/SU893131A3/ru active
- 1977-01-12 FI FI770088A patent/FI63750C/fi not_active IP Right Cessation
- 1977-01-12 PL PL1977195267A patent/PL103074B1/pl unknown
- 1977-01-14 JP JP255077A patent/JPS52116463A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI770088A7 (cs) | 1977-07-15 |
| CS208719B2 (en) | 1981-09-15 |
| PL195267A1 (pl) | 1978-03-13 |
| SU893131A3 (ru) | 1981-12-23 |
| FI63750C (fi) | 1983-08-10 |
| YU7876A (en) | 1982-02-28 |
| FI63750B (fi) | 1983-04-29 |
| JPS52116463A (en) | 1977-09-29 |
| YU39341B (en) | 1984-10-31 |
| JPS5744667B2 (cs) | 1982-09-22 |
| SE7700172L (sv) | 1977-07-15 |
| ATA980876A (de) | 1979-07-15 |
| HU172999B (hu) | 1979-01-28 |
| AT355013B (de) | 1980-02-11 |
| PL103074B1 (pl) | 1979-05-31 |
| SE416730B (sv) | 1981-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |