4-(2-Pyridylamidoethyl)piperidines

Details 4-(2-Pyridylamidoethyl)piperidines 4-(2-Pyridylamidoethyl)piperidines

1975-10-17

1976-11-16

Jiles, Henry R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26029352, 26029356, 26029358, 260295R, 260295AM, 2602955R, 2602955A, 260296R, 424267, C07D21356

Patent

active

039923886

ABSTRACT:
Disclosed herein is an improved process for the preparation of known hypoglycemic piperidinesulfamylureas of the structue ##SPC1##
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 structue ##SPC2##
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: 2712014 (1955-06-01), Suter et al.

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