CN101001839A - 制备n－氨基哌啶及其盐的方法 - Google Patents
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- CN101001839A CN101001839A CNA2005800263491A CN200580026349A CN101001839A CN 101001839 A CN101001839 A CN 101001839A CN A2005800263491 A CNA2005800263491 A CN A2005800263491A CN 200580026349 A CN200580026349 A CN 200580026349A CN 101001839 A CN101001839 A CN 101001839A
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- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 title description 12
- 238000000034 method Methods 0.000 title description 9
- 150000003839 salts Chemical class 0.000 title description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229940083608 sodium hydroxide Drugs 0.000 description 3
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical class CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- UWSDONTXWQOZFN-UHFFFAOYSA-N N-nitrosopiperidine Chemical compound O=NN1CCCCC1 UWSDONTXWQOZFN-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- SXESBRNYONQKLV-UHFFFAOYSA-N n-piperidin-1-ylacetamide Chemical class CC(=O)NN1CCCCC1 SXESBRNYONQKLV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及制备下式(I)N－氨基哌啶的新方法。
Description
本发明主题是制备下式N-氨基哌啶的新方法：
在文献中已知许多制备N-氨基哌啶的方法：
-使用哌啶和氯胺的腊希法；
-使用肼和N-乙酰基氨基哌啶的方法；
-使用N-亚硝基哌啶的方法(Lunn，Keefer，J.Org.Chem.，1984，49(19)，3470)；
-使用戊二醛和苯并三唑的方法(Katritzky A.R.，Wei-Quiang Fan，J.Org.Chem.，1990，55，3205-3209)。
本发明制备N-氨基哌啶(I)及其盐的方法其特征在于：
a)用下式(III)1，5-二卤代戊烷(式中，Hal代表卤素原子)：
Hal-(CH2)5-Hal(IH)
处理下式(II)肼基甲酸酯(carbazate)(式中，R代表(C1-C6)烷基、苯基或苄基)：
NH2-NH-COOR(II)；
b)在酸性介质或碱性介质中处理由此得到的下式哌啶-1-基肼基甲酸酯(其中，R代表(C1-C6)烷基、苯基或苄基)：
以制备所需N-氨基哌啶。
如果需要，可以与无机酸或有机酸反应制备N-氨基哌啶(I)的盐。
术语“卤素原子”是指溴、氯或碘原子。
在室温与溶剂回流温度之间，在溶剂中实施阶段a)，该溶剂例如乙腈或甲苯。
在室温与溶剂回流温度之间，在酸性介质或碱性介质存在下在溶剂中实施阶段b)，该酸性介质例如存在盐酸或氢溴酸，该碱性介质例如存在氢氧化钾或氢氧化钠，该溶剂例如水或乙醇。
根据本发明一个优选具体实施方案，阶段a)中，在乙腈中加热回流溶剂，使用式(III)化合物(式中，Hal代表溴原子)处理式(II)化合物(式中，R代表乙基)。
根据本发明一个优选具体实施方案，阶段b)中，在水中，加热回流溶剂，使用氢氧化钠处理式(IV)化合物(式中，R代表乙基)。
优选，制备N-氨基哌啶的盐，例如氢溴酸盐、氢氯酸盐或草酸盐。例如，可以在溶剂(例如甲基叔丁基醚(MTBE))中制备N-氨基哌啶氢溴酸盐。
实施例
A-哌啶-1-基肼基甲酸乙基酯
制备565.3g的在373ml乙腈中的肼基甲酸乙基酯的混合物。将415.4g 1，5-二溴代戊烷倾倒于上述混合物中，回流。保持回流3小时。真空下通过冷凝除去乙腈。如此得到的残留物溶于甲苯/水混合物中。加入30％NaOH使得该两相混合物pH＝5。沉积并使用甲苯再提取分离水相。将水和36％HCl加入到合并的甲苯相中。使用甲基叔-丁基醚(MTBE)洗该“富含”水相3-4次以除去中性物质(杂质、肼基甲酸二乙基酯、残留二溴代戊烷)。在甲苯存在下，使用NaOH然后使用NaHCO3碱化该酸性水相。使用甲苯再提取水相。使用水洗甲苯相，以消耗残留的肼基甲酸乙基酯。浓缩干燥该甲苯相。通过在甲基环己烷中再结晶纯化该产物，得到252g白色粉末形式的所需产物。
1H NMR(300MHz)：δ(ppm)：1.23：t：3H；4.14：qd：2H；2.70：t：4H；1.66：qt：4H；1.36：qt：2H；5.54：bs：1H。
B-N-氨基哌啶
将160g上述阶段得到的化合物、214ml水和120g氢氧化钠珠的混合物回流3小时，同时使用氩气冲扫。冷却后，再过滤存在的无机物质之前，加入640ml MTBE。得到在MTBE中的粗N-氨基哌啶溶液。
C-制备粗N-氨基哌啶氢溴酸盐
25℃下，于0.5小时内将约1体积36％w/w氢溴酸的乙醇溶液与上述阶段得到的N-氨基哌啶在MTBE中的溶液反应。观察到沉淀的生成，搅拌该混合物1小时。20℃下过滤氢溴酸盐，并使用乙醇然后使用MTBE洗。然后在真空下45-50℃下干燥，得到156g所需化合物。
M.p.＝177-177.5℃(文献174-175℃)。
Claims (7)
1.制备下式N-氨基哌啶及其与无机酸或有机酸的盐的方法：
其特征在于：
a)使用下式(III)1，5-二卤代戊烷，式中Hal代表卤素原子：
Hal-(CH2)5-Hal(III)
处理下式(II)肼基甲酸酯，式中R代表(C1-C6)烷基、苯基或苄基：
NH2-NH-COOR(II)；
b)在酸性介质或碱性介质中处理由此得到的下式哌啶-1-基肼基甲酸酯，其中，R如上所定义：
以得到式(I)化合物。
2.根据权利要求1的方法，其特征在于在阶段a)中，在室温与溶剂回流温度之间在溶剂中实施该反应，其中溶剂选自乙腈或甲苯。
3.根据权利要求1或2的方法，其特征在于在阶段b)中，在室温与溶剂回流温度之间，使用酸或碱在溶剂中实施反应，该酸选自盐酸或氢溴酸，该碱选自氢氧化钾或氢氧化钠，该溶剂例如水或乙醇。
4.根据权利要求1-3任一项的方法，其特征在于阶段a)中，在乙腈中，加热回流溶剂，使用式(III)化合物处理式(II)化合物，式(III)中Hal代表溴原子，式(II)中R代表乙基。
5.根据权利要求1-4任一项的方法，其特征在于阶段b)中，在水中，加热回流溶剂，使用氢氧化钠处理式(IV)化合物，式中R代表乙基。
6.根据权利要求1-5任一项的方法，其特征在于制备式(I)化合物的盐，其选自氢溴酸盐、氢氯酸盐或草酸盐。
7.根据权利要求1-6任一项的方法，其特征在于在甲基叔丁基醚中制备式(I)化合物的氢溴酸盐。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0408700 | 2004-08-05 | ||
| FR0408700A FR2874013B1 (fr) | 2004-08-05 | 2004-08-05 | Procede de preparation de la n-aminopiperidine et de ses sels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101001839A true CN101001839A (zh) | 2007-07-18 |
Family
ID=34947045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2005800263491A Pending CN101001839A (zh) | 2004-08-05 | 2005-08-02 | 制备n－氨基哌啶及其盐的方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20070173648A1 (zh) |
| EP (1) | EP1776341A1 (zh) |
| JP (1) | JP2008509114A (zh) |
| KR (1) | KR20070048765A (zh) |
| CN (1) | CN101001839A (zh) |
| AR (1) | AR050089A1 (zh) |
| AU (1) | AU2005279087A1 (zh) |
| BR (1) | BRPI0514076A (zh) |
| CA (1) | CA2576718A1 (zh) |
| FR (1) | FR2874013B1 (zh) |
| IL (1) | IL180870A0 (zh) |
| MX (1) | MX2007001140A (zh) |
| RU (1) | RU2373196C2 (zh) |
| TW (1) | TW200621713A (zh) |
| UY (1) | UY29045A1 (zh) |
| WO (1) | WO2006024778A1 (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2864081B1 (fr) * | 2003-12-17 | 2006-04-28 | Isochem Sa | Procede de synthese de derives de cycloalkyl-hydrazines exocycliques et de derives d'heterocycloalkyl-hydrazines exocycliques. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE338609C (de) | 1919-10-15 | 1921-06-22 | Fritz Sommer Dr | Verfahren zur Darstellung von Hydrazin und dessen Alkyl- oder Arylsubstitutionsprodukten |
| US3317607A (en) * | 1959-07-30 | 1967-05-02 | Fmc Corp | Chemical reduction of nitrosamines |
| DE4138142C2 (de) * | 1991-11-20 | 1996-04-25 | Cassella Ag | Verfahren zur Herstellung von 1-Amino-2,6-dimethylpiperidin |
| US5977360A (en) * | 1996-12-27 | 1999-11-02 | Japan Hydrazine Co., Ltd. | Process for producing cyclic hydrazine derivatives, tetra-hydropyridazine and hexahydropyridazine |
| JP4118559B2 (ja) * | 2001-12-19 | 2008-07-16 | 日本曹達株式会社 | 脂環式ヒドラジンの製造方法 |
| JP2004137181A (ja) * | 2002-10-17 | 2004-05-13 | Nippon Soda Co Ltd | Ｎ−アミノピペリジンの製造法 |
| JP2004137182A (ja) * | 2002-10-17 | 2004-05-13 | Nippon Soda Co Ltd | Ｎ−アミノピペリジンの製造方法 |
-
2004
- 2004-08-05 FR FR0408700A patent/FR2874013B1/fr not_active Expired - Fee Related
-
2005
- 2005-08-02 KR KR1020077005078A patent/KR20070048765A/ko not_active Withdrawn
- 2005-08-02 CN CNA2005800263491A patent/CN101001839A/zh active Pending
- 2005-08-02 AR ARP050103210A patent/AR050089A1/es active IP Right Grant
- 2005-08-02 CA CA002576718A patent/CA2576718A1/fr not_active Abandoned
- 2005-08-02 WO PCT/FR2005/002016 patent/WO2006024778A1/fr active Application Filing
- 2005-08-02 EP EP05796225A patent/EP1776341A1/fr not_active Withdrawn
- 2005-08-02 UY UY29045A patent/UY29045A1/es not_active Application Discontinuation
- 2005-08-02 RU RU2007107806/04A patent/RU2373196C2/ru not_active IP Right Cessation
- 2005-08-02 JP JP2007524372A patent/JP2008509114A/ja active Pending
- 2005-08-02 BR BRPI0514076-5A patent/BRPI0514076A/pt not_active IP Right Cessation
- 2005-08-02 MX MX2007001140A patent/MX2007001140A/es active IP Right Grant
- 2005-08-02 AU AU2005279087A patent/AU2005279087A1/en not_active Abandoned
- 2005-08-04 TW TW094126537A patent/TW200621713A/zh unknown
-
2007
- 2007-01-22 US US11/625,367 patent/US20070173648A1/en not_active Abandoned
- 2007-01-22 IL IL180870A patent/IL180870A0/en unknown
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2008
- 2008-06-30 US US12/164,379 patent/US7951952B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL180870A0 (en) | 2009-02-11 |
| JP2008509114A (ja) | 2008-03-27 |
| RU2373196C2 (ru) | 2009-11-20 |
| UY29045A1 (es) | 2006-03-31 |
| WO2006024778A1 (fr) | 2006-03-09 |
| FR2874013B1 (fr) | 2006-09-29 |
| FR2874013A1 (fr) | 2006-02-10 |
| AR050089A1 (es) | 2006-09-27 |
| CA2576718A1 (fr) | 2006-03-09 |
| TW200621713A (en) | 2006-07-01 |
| KR20070048765A (ko) | 2007-05-09 |
| RU2007107806A (ru) | 2008-09-10 |
| US20070173648A1 (en) | 2007-07-26 |
| BRPI0514076A (pt) | 2008-05-27 |
| EP1776341A1 (fr) | 2007-04-25 |
| US20080306274A1 (en) | 2008-12-11 |
| AU2005279087A1 (en) | 2006-03-09 |
| US7951952B2 (en) | 2011-05-31 |
| MX2007001140A (es) | 2007-04-19 |
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