GB799779A - Method of producing n-alkyl-alkyl-piperidine monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine monocarboxylic acid amides - Google Patents
Method of producing n-alkyl-alkyl-piperidine monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine monocarboxylic acid amidesInfo
- Publication number
- GB799779A GB799779A GB4584/57A GB458457A GB799779A GB 799779 A GB799779 A GB 799779A GB 4584/57 A GB4584/57 A GB 4584/57A GB 458457 A GB458457 A GB 458457A GB 799779 A GB799779 A GB 799779A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- monocarboxylic acid
- piperidine
- methyl
- pyrrolidine
- 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- -1 chloro-substituted benzene ring Chemical group 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- TVSMLBGFGKLKOO-UHFFFAOYSA-N 1,4-dimethylpiperidine Chemical compound CC1CCN(C)CC1 TVSMLBGFGKLKOO-UHFFFAOYSA-N 0.000 abstract 1
- LPCWDBCEHWHJGX-UHFFFAOYSA-N 1-ethyl-2-methylpiperidine Chemical compound CCN1CCCCC1C LPCWDBCEHWHJGX-UHFFFAOYSA-N 0.000 abstract 1
- LBUPWCHXRSTTNO-UHFFFAOYSA-N 2,2-dimethylpiperidine Chemical compound CC1(C)CCCCN1 LBUPWCHXRSTTNO-UHFFFAOYSA-N 0.000 abstract 1
- RNYFTYLMCRHDRU-UHFFFAOYSA-N 3-methyl-1-propylpyrrolidine Chemical compound CCCN1CCC(C)C1 RNYFTYLMCRHDRU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000001555 benzenes Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Abstract
N - Alkyl - alkyl - piperidine - monocarboxylic acid amides and N-alkyl-alkyl-pyrrolidine monocarboxylic acid amides of the formul\mg <FORM:0799779/IV (b)/1> respectively, wherein R1 is an alkyl group, R2 and R3 are each an alkyl group or one is alkyl and the other is hydrogen, and Ar is an unsubstituted benzene ring or an alkyl, alkoxy, hydroxy and/or chloro-substituted benzene ring, are prepared by reacting an aniline- or appropriately substituted aniline-magnesium halide with an alkyl-pyrrole or -pyrrolidine monocarboxylic acid ester or an alkyl-pyridine or -piperidine monocarboxylic acid ester, which may or may not be N-alkylated, hydrolysing the reaction product with an acid and, when necessary, hydrogenating the heterocyclic ring and alkylating the nuclear nitrogen atom. Preferred aniline magnesium halides are those in which Ar is substituted with an alkyl group or chlorine in the 2-position, with or without a hydroxy, alkyl or alkoxy group in the 4-position and with or without chlorine or an alkyl or alkoxy group in the 6-position. The examples describe the preparation of N-methyl-4-methyl-piperidine - a - monocarboxylic acid - 2 : 6 - dimethyl - anilide, N - ethyl - 6 - methyl - piperidine - b - monocarboxylic acid - 2 - ethyl anilide, N - n - propyl - 4 - methyl-pyrrolidine - a - monocarboxylic acid-2 : 6-dimethyl anilide and N-methyl - 4 : 6 - dimethyl - piperidine - a - monocarboxylic acid - 2 - methyl - 6 - chloro - anilide. Specifications 799,778 and 799,780 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE799779X | 1956-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB799779A true GB799779A (en) | 1958-08-13 |
Family
ID=20339855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4584/57A Expired GB799779A (en) | 1956-02-22 | 1957-02-11 | Method of producing n-alkyl-alkyl-piperidine monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine monocarboxylic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB799779A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3038835A (en) * | 1959-07-01 | 1962-06-12 | Bofors Ab | Method for the production of lowtoxic surface anaesthetics |
-
1957
- 1957-02-11 GB GB4584/57A patent/GB799779A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3038835A (en) * | 1959-07-01 | 1962-06-12 | Bofors Ab | Method for the production of lowtoxic surface anaesthetics |
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