Process for the synthesis of 4-(2-pyridylamido ethyl) piperidine

Details Process for the synthesis of 4-(2-pyridylamido ethyl) piperidine Process for the synthesis of 4-(2-pyridylamido ethyl) piperidine

1974-09-10

1976-01-20

Winters, Sherman D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26029356, 26029358, 26029369, 260295R, 260295AM, 2602955R, 2602955A, 260296R, 424267, C07D21102

Patent

active

039338304

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 sulfonamides produced by the process of the instant invention are converted to the desired hypoglycemic agent by methods well-known to those skilled in the art.
The 4-(2-pyridylamidoethyl)pyridines and piperidines of the instant invention are themselves novel compounds useful as intermediates in the synthesis of piperidine sulfamylurea hypoglycemic agents.

REFERENCES:
patent: 3794652 (1974-02-01), Naito
patent: 3829434 (1974-08-01), Evanega et al.
patent: 3886167 (1975-05-01), Ash et al.
Freifelder, Advances in Catalysis 14 : 203 - 253 (1963).
J.A.C.S. 79 : 472 - 480 (1957), McCarty et al.

Affiliated with

Also associated with

Rating

Process for the synthesis of 4-(2-pyridylamido ethyl) piperidine does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the synthesis of 4-(2-pyridylamido ethyl) piperidine, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the synthesis of 4-(2-pyridylamido ethyl) piperidine will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1697114