SU867298A3 - Способ получени производных пиперидина или их солей - Google Patents
Способ получени производных пиперидина или их солей Download PDFInfo
- Publication number
- SU867298A3 SU867298A3 SU772534004A SU2534004A SU867298A3 SU 867298 A3 SU867298 A3 SU 867298A3 SU 772534004 A SU772534004 A SU 772534004A SU 2534004 A SU2534004 A SU 2534004A SU 867298 A3 SU867298 A3 SU 867298A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzoyl
- salts
- group
- piperidine derivatives
- piperidine
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
содержат 1-6 углеродных атомов, пред почтительно 1-4 углеродных атома. Низшие алкилокси-группыЬ могут содер жать 1-4 атома углерода. Гидролиз соединений формулы I I целесообразно проводить в органическом растворителе (например, низший спирт, предпочтительно метанол,этанол или циклический эфир, например диоксан или тетрагидрофуран) в присутствии минеральной кислоты или избытка гидроокиси щелочного метала при температурах от до темпера±уры кипени растворител . Пример. 4-Феноксиметилпи- перидин. Смесь, состо щую из 22,0 г (0,075 моль) м-6ензоил-4-феноксиметилпиперидина , 25 мл 10 н. гидроокиси натри и 175 мл этанола, кип т т в течение 18 ч с обратным холодильником, после чего упаривают в вакууме, разбавл ют эфиром, промывают водой, высушивают над сульфатом натри и упаривают раст воритель. Получают 12,0 г (84%) 4-феноксиметилпиперидина ,. с с Тпд42-43 Испольэуемый в качестве исходного соединени Ы-бензоил-4-феноксиметилпиперидин получают следующим образом Смесь, состо щую из 135 г М-бензоил-4-оксиметилпиперидина (Tц 83-85°С ), полученного- из 4-оксиметил пиперидина и бензоилхлорида (4-окси- ;метилпиперидин получают гидрированием 4-оксиметилпиридина в мотанолр при 140°С и давлении водорода 200 ат в присутствии окиси рутени , Т уопри 14 мм рт. ст. 12б-130С, Тг,д ЗБ-бб С). 90 мл тионилхлорида и 900 мл хлороформа кип т - 4 ч с обратным холодильником . Затем добавл ют воды при охлаждении льдом, промывают органическую фазу раствором гидрокарбоната натри до нейтральной реакции, высушивают над сульфатом натри и упаривают . Получают 132,0 г N-бензоил-4-хлорметилпиперидинас (90% от теории ) с Тпл 68-70 С. К смеси, состо щей из 28 мл 30%ного раствора метилата на1;ри и 50 мл метанола, добавл ют 14,1 г (0,15 моль) фенола, упаривают в вакууме, остаток раствор ют в 120 мл N,N-диметилформамида , добавл ют 35,5 г (0,15 моль) М-бензоил-4-хлорметилпиперидина и перемешивают 12 ч при 60-70 0. После охлаждени разбавл ют эфиром, промывают водой и разбавленным раствором гидроокиси натри , высушивают над сульфатом натри и упаривают в вакууме . Маслообразный остаток растирают со смесью эфира с лигроином. Получают 23,0 г М-бензоил-4-феноксиметил-пиперидина (52% от теории) с Tj,95-96°C. Аналогичным образом получают другие производные пиперидинд , приведенные в таблице.
П р и м е р 2. 4-Феноксимети;7ПИперидин .
Смесь 18,7 г( 0,08 моль) N-ацетил-4-феноксиметилпиперидина , 24 мл 10 н. NaOH и 160 мл этанола нагревают 18 ч при дефлегмации, концентрируют , перенос т в воду и экстрагируют эфиром. После перегонки выдел ют 13,0 г 4-феноксиметилпиперидина (85% от теории) , Тщщ при 0,05 мм рт. ст, 107-112, Тр. 3940С .
Claims (1)
1. Способ получени производных пиперидина общей формулы I
Hf(CHg 0где R - водород, галоген, низша алкильна группа, низша алкокси- группа или нитро- группа, или их солей, заключающийс в том,что N-замещенное производное 4-фенокси- э метилпиридина общей формулы II
в-|- Г)-сн.-о-(
где R - имеет указанное значение} R - низша алкильна или арильна группа или низша алкилокси- или арилокси- группа, подвергают гидролизу в кислой или щелочной среде с последующим выделением целевого продукта в свободном виде или в виде соли.
Источники информации, прин тие во внимание при экспертизе. 20 1. Физер Л. и Физер М. Органическа хими , 1966, с. 340.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752549999 DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU867298A3 true SU867298A3 (ru) | 1981-09-23 |
Family
ID=5961166
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762415648A SU633473A3 (ru) | 1975-11-07 | 1976-11-02 | Способ получени производных пиперидина или их солей |
| SU772534004A SU867298A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
| SU772534003A SU662009A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762415648A SU633473A3 (ru) | 1975-11-07 | 1976-11-02 | Способ получени производных пиперидина или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772534003A SU662009A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4243807A (ru) |
| JP (1) | JPS6055509B2 (ru) |
| AT (1) | AT352726B (ru) |
| BE (1) | BE847973A (ru) |
| CA (1) | CA1077942A (ru) |
| CH (3) | CH624102A5 (ru) |
| DD (1) | DD126942A5 (ru) |
| DE (1) | DE2549999A1 (ru) |
| DK (1) | DK494876A (ru) |
| FI (1) | FI763148A (ru) |
| FR (1) | FR2330678A1 (ru) |
| GB (1) | GB1502050A (ru) |
| HU (1) | HU171237B (ru) |
| IE (1) | IE43866B1 (ru) |
| IT (1) | IT1063618B (ru) |
| LU (1) | LU76141A1 (ru) |
| NL (1) | NL7612286A (ru) |
| SE (1) | SE7612234L (ru) |
| SU (3) | SU633473A3 (ru) |
| ZA (1) | ZA766381B (ru) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| US4556664A (en) * | 1984-03-13 | 1985-12-03 | Gunnar A. K. Aberg | Method and composition for the treatment of cardiac arrhythmias |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| US5231184A (en) * | 1987-11-23 | 1993-07-27 | Janssen Pharmaceutica N.V. | Pridazinamine derivatives |
| US4822778A (en) * | 1988-01-19 | 1989-04-18 | Gunnar Aberg | Membrane stabilizing phenoxy-piperidine compounds and pharmaceutical compositions employing such compounds |
| US5109002A (en) * | 1989-09-08 | 1992-04-28 | Du Pont Merck Pharmaceutical Company | Antipsychotic 1-cycloalkylpiperidines |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| IL99537A (en) * | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical preparations containing them |
| US5264420A (en) * | 1990-09-27 | 1993-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| FR2667317B1 (fr) * | 1990-10-02 | 1992-12-04 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| HUT68769A (en) * | 1991-05-07 | 1995-07-28 | Merck & Co Inc | FIBRINOGéN RECEPTOR ANTAGONIST COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM AS EFFECTIVE SUBSTANCE |
| US5321034A (en) * | 1991-05-07 | 1994-06-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5416099A (en) * | 1991-10-29 | 1995-05-16 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5389631A (en) * | 1991-10-29 | 1995-02-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5272158A (en) * | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| CA2144763A1 (en) * | 1992-10-14 | 1994-04-28 | George D. Hartman | Fibrinogen receptor antagonists |
| US5358956A (en) * | 1992-10-14 | 1994-10-25 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| CA2150550A1 (en) * | 1992-12-01 | 1994-06-09 | Melissa S. Egbertson | Fibrinogen receptor antagonists |
| US5441952A (en) * | 1993-04-05 | 1995-08-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5397791A (en) * | 1993-08-09 | 1995-03-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5821241A (en) * | 1994-02-22 | 1998-10-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5719144A (en) * | 1995-02-22 | 1998-02-17 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5750147A (en) | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| KR100403246B1 (ko) * | 1995-09-28 | 2004-02-11 | 가켄 세이야쿠 가부시키가이샤 | ４-메틸렌피페리딘의제조방법 |
| US5789421A (en) * | 1995-10-26 | 1998-08-04 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5780480A (en) * | 1996-02-28 | 1998-07-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5889023A (en) * | 1996-05-10 | 1999-03-30 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5981584A (en) * | 1997-02-06 | 1999-11-09 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| TWI438190B (zh) * | 2008-07-24 | 2014-05-21 | Theravance Inc | ３－（苯氧基苯基甲基）吡咯啶化合物 |
| KR101656339B1 (ko) | 2008-11-14 | 2016-09-09 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | 4［2（2플루오로페녹시메틸）페닐］피페리딘 화합물 |
| JP2012524098A (ja) * | 2009-04-15 | 2012-10-11 | セラヴァンス， インコーポレーテッド | ３−（フェノキシピロリジン−３−イル−メチル）ヘテロアリール、３−（フェニルピロリジン−３−イルメトキシ）ヘテロアリールおよび３−（ヘテロアリールピロリジン−３−イルメトキシ）ヘテロアリール化合物 |
| KR20120070561A (ko) | 2009-07-13 | 2012-06-29 | 세라밴스 인코포레이티드 | 3-페녹시메틸피롤리딘 화합물 |
| US8273786B2 (en) * | 2009-07-21 | 2012-09-25 | Theravance, Inc. | 3-phenoxymethylpyrrolidine compounds |
| WO2011085291A1 (en) * | 2010-01-11 | 2011-07-14 | Theravance, Inc. | 1 - (2 - phenoxymethylphenyl) piperazine compounds as serotonin and norepinephrine reuptake inhibitors |
| EP2550252B1 (en) * | 2010-03-22 | 2015-05-06 | Theravance Biopharma R&D IP, LLC | 1-(2-phenoxymethylheteroaryl)piperidine and piperazine compounds |
| CN103153950B (zh) | 2010-10-11 | 2015-11-25 | 施万生物制药研发Ip有限责任公司 | 血清素再摄取抑制剂 |
| WO2012075239A1 (en) | 2010-12-03 | 2012-06-07 | Theravance, Inc. | Serotonin reuptake inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268951A (en) * | 1969-06-12 | 1972-03-29 | Pfizer Ltd | Phenoxy-amines |
| DE2245061A1 (de) * | 1972-09-14 | 1974-03-28 | Boehringer Mannheim Gmbh | Derivate des adenins |
| DE2401254A1 (de) * | 1974-01-11 | 1975-11-27 | Boehringer Mannheim Gmbh | Neue derivate von n hoch 6-substituierten adeninen |
| DE2550000A1 (de) * | 1975-11-07 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue purin-derivate und verfahren zu ihrer herstellung |
-
1975
- 1975-11-07 DE DE19752549999 patent/DE2549999A1/de active Granted
-
1976
- 1976-10-25 ZA ZA766381A patent/ZA766381B/xx unknown
- 1976-10-28 CA CA264,608A patent/CA1077942A/en not_active Expired
- 1976-10-29 IE IE2394/76A patent/IE43866B1/en unknown
- 1976-11-01 US US05/737,518 patent/US4243807A/en not_active Expired - Lifetime
- 1976-11-01 HU HU76BO00001639A patent/HU171237B/hu not_active IP Right Cessation
- 1976-11-02 DK DK494876A patent/DK494876A/da not_active Application Discontinuation
- 1976-11-02 SU SU762415648A patent/SU633473A3/ru active
- 1976-11-03 SE SE7612234A patent/SE7612234L/xx not_active Application Discontinuation
- 1976-11-03 CH CH1385576A patent/CH624102A5/de not_active IP Right Cessation
- 1976-11-03 FI FI763148A patent/FI763148A/fi not_active Application Discontinuation
- 1976-11-04 GB GB45916/76A patent/GB1502050A/en not_active Expired
- 1976-11-04 BE BE172068A patent/BE847973A/xx not_active IP Right Cessation
- 1976-11-04 DD DD195610A patent/DD126942A5/xx unknown
- 1976-11-05 FR FR7633389A patent/FR2330678A1/fr active Granted
- 1976-11-05 LU LU76141A patent/LU76141A1/xx unknown
- 1976-11-05 JP JP51133139A patent/JPS6055509B2/ja not_active Expired
- 1976-11-05 IT IT29083/76A patent/IT1063618B/it active
- 1976-11-05 AT AT823776A patent/AT352726B/de not_active IP Right Cessation
- 1976-11-05 NL NL7612286A patent/NL7612286A/xx not_active Application Discontinuation
-
1977
- 1977-10-21 SU SU772534004A patent/SU867298A3/ru active
- 1977-10-21 SU SU772534003A patent/SU662009A3/ru active
-
1980
- 1980-10-03 CH CH742480A patent/CH627166A5/de not_active IP Right Cessation
- 1980-10-03 CH CH742380A patent/CH625788A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2549999C2 (ru) | 1989-01-26 |
| GB1502050A (en) | 1978-02-22 |
| IE43866L (en) | 1977-05-07 |
| IT1063618B (it) | 1985-02-11 |
| CH624102A5 (ru) | 1981-07-15 |
| CA1077942A (en) | 1980-05-20 |
| BE847973A (fr) | 1977-05-04 |
| FR2330678A1 (fr) | 1977-06-03 |
| NL7612286A (nl) | 1977-05-10 |
| JPS5259163A (en) | 1977-05-16 |
| SU633473A3 (ru) | 1978-11-15 |
| AT352726B (de) | 1979-10-10 |
| FI763148A (ru) | 1977-05-08 |
| DD126942A5 (ru) | 1977-08-24 |
| ZA766381B (en) | 1977-10-26 |
| US4243807A (en) | 1981-01-06 |
| IE43866B1 (en) | 1981-06-17 |
| ATA823776A (de) | 1979-03-15 |
| CH625788A5 (ru) | 1981-10-15 |
| CH627166A5 (ru) | 1981-12-31 |
| DE2549999A1 (de) | 1977-05-12 |
| HU171237B (hu) | 1977-12-28 |
| DK494876A (da) | 1977-05-08 |
| SE7612234L (sv) | 1977-05-07 |
| FR2330678B1 (ru) | 1980-11-07 |
| JPS6055509B2 (ja) | 1985-12-05 |
| SU662009A3 (ru) | 1979-05-05 |
| LU76141A1 (ru) | 1977-05-18 |
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