CA2167406A1 - A process for the preparation of n,n'-dibenzylbispidine - Google Patents
A process for the preparation of n,n'-dibenzylbispidineInfo
- Publication number
- CA2167406A1 CA2167406A1 CA002167406A CA2167406A CA2167406A1 CA 2167406 A1 CA2167406 A1 CA 2167406A1 CA 002167406 A CA002167406 A CA 002167406A CA 2167406 A CA2167406 A CA 2167406A CA 2167406 A1 CA2167406 A1 CA 2167406A1
- Authority
- CA
- Canada
- Prior art keywords
- dibenzylbispidine
- solvent
- benzylpiperidone
- dibenzylbispidone
- reaction
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000008569 process Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 7
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims abstract description 18
- MLEGMEBCXGDFQT-UHFFFAOYSA-N 1-benzylpiperidin-2-one Chemical compound O=C1CCCCN1CC1=CC=CC=C1 MLEGMEBCXGDFQT-UHFFFAOYSA-N 0.000 claims abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000007792 addition Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229960004279 formaldehyde Drugs 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- DLNAKYFPFYUBDR-HDICACEKSA-N (4-aminophenyl)-[(1s,5r)-7-benzyl-3,7-diazabicyclo[3.3.1]nonan-3-yl]methanone Chemical compound C1=CC(N)=CC=C1C(=O)N1C[C@@H](CN(CC=2C=CC=CC=2)C2)C[C@@H]2C1 DLNAKYFPFYUBDR-HDICACEKSA-N 0.000 description 2
- 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229950005516 ambasilide Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229940093932 potassium hydroxide Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4324086A DE4324086A1 (de) | 1993-07-17 | 1993-07-17 | Verfahren zur Herstellung von N,N`-Dibenzylbispidin |
| DEP4324086.0 | 1993-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2167406A1 true CA2167406A1 (en) | 1995-01-26 |
Family
ID=6493125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002167406A Abandoned CA2167406A1 (en) | 1993-07-17 | 1994-06-28 | A process for the preparation of n,n'-dibenzylbispidine |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0710238A1 (ja) |
| JP (1) | JPH09500119A (ja) |
| KR (1) | KR960703913A (ja) |
| AU (1) | AU7073394A (ja) |
| CA (1) | CA2167406A1 (ja) |
| CZ (1) | CZ5296A3 (ja) |
| DE (1) | DE4324086A1 (ja) |
| HU (1) | HU9503859D0 (ja) |
| MX (1) | MX9405030A (ja) |
| PL (1) | PL312609A1 (ja) |
| WO (1) | WO1995002599A1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115626925A (zh) * | 2022-12-08 | 2023-01-20 | 山东汇海医药化工有限公司 | 一种双哌啶的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2428792A1 (de) * | 1974-06-14 | 1976-01-02 | Knoll Ag | Neue antiarrhythmika |
-
1993
- 1993-07-17 DE DE4324086A patent/DE4324086A1/de not_active Withdrawn
-
1994
- 1994-06-28 EP EP94919667A patent/EP0710238A1/de not_active Withdrawn
- 1994-06-28 HU HU9503859A patent/HU9503859D0/hu unknown
- 1994-06-28 AU AU70733/94A patent/AU7073394A/en not_active Abandoned
- 1994-06-28 CZ CZ9652A patent/CZ5296A3/cs unknown
- 1994-06-28 CA CA002167406A patent/CA2167406A1/en not_active Abandoned
- 1994-06-28 KR KR1019960700211A patent/KR960703913A/ko not_active Application Discontinuation
- 1994-06-28 WO PCT/EP1994/002101 patent/WO1995002599A1/de not_active Application Discontinuation
- 1994-06-28 JP JP7504314A patent/JPH09500119A/ja active Pending
- 1994-06-28 PL PL94312609A patent/PL312609A1/xx unknown
- 1994-07-01 MX MX9405030A patent/MX9405030A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL312609A1 (en) | 1996-04-29 |
| AU7073394A (en) | 1995-02-13 |
| EP0710238A1 (de) | 1996-05-08 |
| HU9503859D0 (en) | 1996-02-28 |
| KR960703913A (ko) | 1996-08-31 |
| CZ5296A3 (en) | 1996-04-17 |
| MX9405030A (es) | 1995-01-31 |
| JPH09500119A (ja) | 1997-01-07 |
| DE4324086A1 (de) | 1995-01-19 |
| WO1995002599A1 (de) | 1995-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2001503388A (ja) | メトプロロールの新規な製造方法 | |
| US4322359A (en) | Process for the preparation of 2,5-dimethyl-1,4: 3,6-dianhydrosorbitol | |
| EP0764630B1 (en) | Process for the preparation of dialkyl succinylsuccinates | |
| CN108864084B (zh) | 一组阿哌沙班有关物质及其制备方法 | |
| CA2167406A1 (en) | A process for the preparation of n,n'-dibenzylbispidine | |
| IE49091B1 (en) | A novel process for the preparation of 2',6'-dialkyl-n-alkoxymethyl-2-chloro-acetanilides | |
| US5026852A (en) | Process for the preparation of cytosines | |
| EP0260588B1 (en) | Process for the preparation of alpha-N-[(hypoxanthin-9-yl)-pentyloxycarbonyl]-arginine | |
| IL153424A (en) | Process for preparing quinoline derivatives | |
| KR20010005943A (ko) | 0-(3-아미노-2-히드록시-프로필)-히드록심산할라이드의 제조방법 | |
| GB1597428A (en) | Manufacture of pyridoxin | |
| KR840000115B1 (ko) | 카바졸 유도체의 제조방법 | |
| FR2493316A1 (fr) | Nouveau procede de preparation des (trialcoxy benzyl)-1 piperazines et notamment de la (trimethoxy-2', 3', 4' benzyl)-1 piperazine | |
| KR20050096121A (ko) | 수용성 β-하이드록시니트릴의 제조 방법 | |
| US4751314A (en) | Preparation of tetrachloro-3-iminoisoindolin-1-one | |
| US6407219B1 (en) | Process for preparing azoiminoethers and azocarboxylic acid esters and novel azocboxylic acid mixed esters | |
| JPS60132933A (ja) | ニトロジアリ‐ルアミンの製造方法 | |
| US5616723A (en) | Process for the preparation of 3-amino-5-methylpyrazole | |
| JPH0115504B2 (ja) | ||
| KR800001178B1 (ko) | 아세토 나이트릴유도체의 제조방법 | |
| JP2717995B2 (ja) | １，２，３−トリアゾールの製法 | |
| EP0402561B1 (en) | Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof | |
| JP3876933B2 (ja) | 硫酸水素エステルの製造方法 | |
| EP0104721B1 (en) | Process for the preparation of 2-chlorosulfonyl-4-(n-substituted sulfamyl)-chlorobenzene compounds | |
| JP2002155058A (ja) | １位置換ヒダントイン類の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |