Process for the synthesis of 4-(2-pyridylamido ethyl) piperidines
US3933830A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 10, 1974 |
| Grant date | Jan 20, 1976 |
| Priority date | — |
| Expiry date | Sep 10, 1994 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D401/12
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
Disclosed herein is an improved process for the preparation of known hypoglycemic piperidinesulfamylureas of the structure ##EQU1## wherein R is selected from the group consisting of 3-(2-methoxy)pyridyl, 3-(2-ethoxy)pyridyl and 2-(4-chloro)pyridyl and R' is selected from the group consisting of bicyclo[2.2.1]hept-5-en-2-yl-endo-methyl, bicyclo[2.2.1]hept-2-yl-endo-methyl, 7-oxabicyclo[2.2.1]hept-2-yl-methyl, 1-adamantyl and cycloalkyl having from five to eight carbon atoms. Said process comprises contacting 4-(2-pyridyl-amidoethyl) piperidine of the structure ##EQU2## with substantially one equivalent of sulfamide thereby exclusively sulfonating the piperidine nitrogen atom. Said 4-(2-pyridylamidoethyl)piperidines from the corresponding 4-(2-pyridylamidoethyl) pyridines by selectively activating the more basic nitrogen atom of said pyridine compound either by N-alkylation or by contact with acid and then exclusively reducing the activated pyridine ring with either hydrogen alone or in combination with a metal hydride. Said 4-(2-pyridylamidoethyl)pyridines are produced by contacting 4-(2-aminoethyl)pyridine with a pyridyl acid chloride of the formula R(C=O)Cl. The piperidine sulfon…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.