GB775750A - Method of preparing amides of n-alkyl piperidine mono-carboxylic acid and n-alkyl pyrrolidine -a-monocarboxylic acid - Google Patents
Method of preparing amides of n-alkyl piperidine mono-carboxylic acid and n-alkyl pyrrolidine -a-monocarboxylic acidInfo
- Publication number
- GB775750A GB775750A GB20714/55A GB2071455A GB775750A GB 775750 A GB775750 A GB 775750A GB 20714/55 A GB20714/55 A GB 20714/55A GB 2071455 A GB2071455 A GB 2071455A GB 775750 A GB775750 A GB 775750A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- give
- alkylated
- prepared
- alkyl group
- 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.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 title abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- -1 aniline magnesium halide Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- JSHASCFKOSDFHY-UHFFFAOYSA-N 1-butylpyrrolidine Chemical compound CCCCN1CCCC1 JSHASCFKOSDFHY-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- ZICBNHLULHJETL-UHFFFAOYSA-N ethyl 1-methylpiperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C ZICBNHLULHJETL-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 abstract 1
- BPSLZWSRHTULGU-UHFFFAOYSA-N Methylpipecolic acid Chemical compound CN1CCCCC1C(O)=O BPSLZWSRHTULGU-UHFFFAOYSA-N 0.000 abstract 1
- VUHKTERBGMWQAY-UHFFFAOYSA-N N-(2-ethylphenyl)-1-propan-2-ylpiperidine-3-carboxamide Chemical compound C(C)C1=C(NC(C2CN(CCC2)C(C)C)=O)C=CC=C1 VUHKTERBGMWQAY-UHFFFAOYSA-N 0.000 abstract 1
- BOYAEDAIOHNLKU-UHFFFAOYSA-L [Br-].[Mg+2].ClC1=C(N)C(=CC=C1)C.[Br-] Chemical compound [Br-].[Mg+2].ClC1=C(N)C(=CC=C1)C.[Br-] BOYAEDAIOHNLKU-UHFFFAOYSA-L 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 abstract 1
- 229910001623 magnesium bromide Inorganic materials 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- DNZSDACGXYHMOL-UHFFFAOYSA-N n-(2-ethylphenyl)piperidine-3-carboxamide Chemical compound CCC1=CC=CC=C1NC(=O)C1CNCCC1 DNZSDACGXYHMOL-UHFFFAOYSA-N 0.000 abstract 1
- GUTOQBOCGOYORW-UHFFFAOYSA-N n-methyl-n-phenylpiperidine-4-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1CCNCC1 GUTOQBOCGOYORW-UHFFFAOYSA-N 0.000 abstract 1
- FCTZHFATVFONMW-UHFFFAOYSA-N n-phenylpyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC1=CC=CC=C1 FCTZHFATVFONMW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
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
- C07D211/36—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 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Amides of the general formul <FORM:0775750/IV(b)/1> and <FORM:0775750/IV(b)/2> wherein R1 is an alkyl group, R2 an alkyl group of 1-5 carbon atoms or chlorine, R3 a hydrogen atom, an alkyl group of 1-5 carbon atoms, an alkoxy or a hydroxy group, and R4 a hydrogen atom, chlorine, an alkyl group of 1-5 carbon atoms or an alkoxy group, or in which R2, R3 and R4 are all hydrogen, are prepared by reacting an appropriately substituted aniline magnesium halide with the appropriate pyridine, piperidine, pyrrole or pyrrolidine monocarboxylic acid ester, which may or may not be N-alkylated, hydrolysing the reaction product and, where required, hydrogenating the heterocyclic ring and alkylating the nitrogen atom thereof. In the examples: (1) ethyl magnesium bromide and 2 : 6-dimethylaniline give 2 : 6-dimethylaniline magnesium bromide, this is refluxed with N-methylpipecolic acid ethyl ester and the product on hydrolysis with dilute Hcl gives N-methylpipecolic acid 2 : 6-dimethylanilide; (2) nipecotic acid 2-ethylanilide, prepared as in example (1), is alkylated with isopropyl bromide to give N-isopropylnipecotic acid 2-ethylanilide; (3) isonicotinic acid anilide, prepared as in example (1), is catalytically hydrogenated and the product is alkylated with dimethyl sulphate to give N-methylisonipecotic acid anilide; (4) 2-chloro-6-methylaniline magnesium bromide and N-n-butylpyrrolidine a -carboxylic acid ester give N-n-butylpyrrolidine a -carboxylic acid 2-chloro-6-methylanilide; (5) pipecolinyl - 2 : 4 : 6 - trimethylanilide, prepared as in example (1), is alkylated with diethyl sulphate to give N-ethylpipecolinyl-2 : 4 : 6-trimethylanilide; (6) 2 : 6 - dimethyl - 4 - butoxyaniline magnesium bromide and N-methylpipecolinic acid ethyl ester give N-methylpipecolinyl - 2 : 6 - dimethyl - 4 - butoxyanilide. Specifications 770,129 and 772,807 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE775750X | 1955-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB775750A true GB775750A (en) | 1957-05-29 |
Family
ID=20333465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20714/55A Expired GB775750A (en) | 1955-04-28 | 1955-07-18 | Method of preparing amides of n-alkyl piperidine mono-carboxylic acid and n-alkyl pyrrolidine -a-monocarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB775750A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
| WO2010084516A1 (en) * | 2009-01-23 | 2010-07-29 | Jubilant Organosys Limited | Process for producing optically active n-alkyl-piperidine-2-carboxanilide |
| CN104003930A (en) * | 2014-06-13 | 2014-08-27 | 山东阿如拉药物研究开发有限公司 | Method for preparing hydrochloric acid ropivacaine |
-
1955
- 1955-07-18 GB GB20714/55A patent/GB775750A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
| WO2010084516A1 (en) * | 2009-01-23 | 2010-07-29 | Jubilant Organosys Limited | Process for producing optically active n-alkyl-piperidine-2-carboxanilide |
| CN104003930A (en) * | 2014-06-13 | 2014-08-27 | 山东阿如拉药物研究开发有限公司 | Method for preparing hydrochloric acid ropivacaine |
| CN104003930B (en) * | 2014-06-13 | 2016-06-08 | 山东金诃药物研究开发有限公司 | The preparation method of a kind of hydrochloric acid ropivacaine |
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