CN101531628B - 4-二甲胺基哌啶盐酸盐的合成方法 - Google Patents
4-二甲胺基哌啶盐酸盐的合成方法 Download PDFInfo
- Publication number
- CN101531628B CN101531628B CN2009100112006A CN200910011200A CN101531628B CN 101531628 B CN101531628 B CN 101531628B CN 2009100112006 A CN2009100112006 A CN 2009100112006A CN 200910011200 A CN200910011200 A CN 200910011200A CN 101531628 B CN101531628 B CN 101531628B
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- CN
- China
- Prior art keywords
- dimethylamino
- hydrochloride
- piperidine hydrochloride
- still
- compound method
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 23
- IDCJGSDAPFXTGB-UHFFFAOYSA-N n,n-dimethylpiperidin-4-amine;hydrochloride Chemical compound Cl.CN(C)C1CCNCC1 IDCJGSDAPFXTGB-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000001953 recrystallisation Methods 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 7
- GJQNVZVOTKFLIU-UHFFFAOYSA-N piperidin-1-ium-4-one;chloride Chemical compound Cl.O=C1CCNCC1 GJQNVZVOTKFLIU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 4
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000006073 displacement reaction Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000002390 rotary evaporation Methods 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
- 238000007792 addition Methods 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 238000007259 addition reaction Methods 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000012264 purified product Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- XESLSYPFOYZAPG-UHFFFAOYSA-N piperidin-1-ium-2-one;chloride Chemical compound Cl.O=C1CCCCN1 XESLSYPFOYZAPG-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- -1 4-dimethylamino-piperidine compound Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- YFJAIURZMRJPDB-UHFFFAOYSA-N n,n-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCNCC1 YFJAIURZMRJPDB-UHFFFAOYSA-N 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical class NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100112006A CN101531628B (zh) | 2009-04-17 | 2009-04-17 | 4-二甲胺基哌啶盐酸盐的合成方法 |
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CN2009100112006A CN101531628B (zh) | 2009-04-17 | 2009-04-17 | 4-二甲胺基哌啶盐酸盐的合成方法 |
Publications (2)
Publication Number | Publication Date |
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CN101531628A CN101531628A (zh) | 2009-09-16 |
CN101531628B true CN101531628B (zh) | 2012-01-11 |
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CN2009100112006A Active CN101531628B (zh) | 2009-04-17 | 2009-04-17 | 4-二甲胺基哌啶盐酸盐的合成方法 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103254121B (zh) * | 2013-04-08 | 2015-08-26 | 洛阳师范学院 | 一种合成(3r,4r)-n-pg-4-甲基-3-甲胺基哌啶的方法 |
CN104592097A (zh) * | 2015-01-21 | 2015-05-06 | 苏州飞翔新材料研究院有限公司 | 一种己二胺哌啶的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3063996A (en) * | 1959-03-02 | 1962-11-13 | Smith Kline French Lab | Substituted piperidinylalkyl phenothiazines |
US5442044A (en) * | 1991-01-04 | 1995-08-15 | Pfizer Inc. | Orally active renin inhibitors |
EP1564212A1 (en) * | 2002-10-02 | 2005-08-17 | Ragactives, S.L. | Method and intermedia used to obtain derivatives of 1-(1h- benzimidazole-2-yl)-4-(2-aminopyrimidine)piperidine |
CN1826340A (zh) * | 2003-05-21 | 2006-08-30 | 普罗西迪恩有限公司 | 作为糖原磷酸化酶抑制剂的吡咯并吡啶-2-甲酸酰胺 |
CN1894259A (zh) * | 2003-08-22 | 2007-01-10 | 活跃生物工艺学公司 | 利福霉素类似物及其应用 |
-
2009
- 2009-04-17 CN CN2009100112006A patent/CN101531628B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3063996A (en) * | 1959-03-02 | 1962-11-13 | Smith Kline French Lab | Substituted piperidinylalkyl phenothiazines |
US5442044A (en) * | 1991-01-04 | 1995-08-15 | Pfizer Inc. | Orally active renin inhibitors |
EP1564212A1 (en) * | 2002-10-02 | 2005-08-17 | Ragactives, S.L. | Method and intermedia used to obtain derivatives of 1-(1h- benzimidazole-2-yl)-4-(2-aminopyrimidine)piperidine |
CN1826340A (zh) * | 2003-05-21 | 2006-08-30 | 普罗西迪恩有限公司 | 作为糖原磷酸化酶抑制剂的吡咯并吡啶-2-甲酸酰胺 |
CN1894259A (zh) * | 2003-08-22 | 2007-01-10 | 活跃生物工艺学公司 | 利福霉素类似物及其应用 |
Non-Patent Citations (2)
Title |
---|
Bernd Peschke et al.The influence of conformational restriction in the C-terminus of growth hormone secretagogues on their potency.《European Journal of Medicinal Chemistry》.2002,第37卷487-501. * |
Sachin S. Diwan et al.Cheap,Efficient,and Scalable Synthesis of 4-N,N-Dimethylaminopiperidine.《Synthetic Communications》.2009,第39卷(第2期),273-277. * |
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CN101531628A (zh) | 2009-09-16 |
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Effective date of registration: 20160901 Address after: 116600 Dalian economic and Technological Development Zone, northeast street, No. 488, Liaoning Patentee after: Dalian nine Fine Chemical Co., Ltd. Address before: 116620 high tech Industrial Park, Liaoning, Dalian double port D double D Street No. 18, No. five Patentee before: Dalian Chemphy Fine Chemical Co., Ltd. |