V. Kuznetsov, S. V. Lantsetov, E. N. Andreeva
Jul 1, 1994
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Journal
Pharmaceutical Chemistry Journal
Abstract
Interest in chemical derivatives of 4-aminopiperidines is due to their broad spectrum of biological activity [1, 2]. During the course of work [5] to prepare and study the biological activity of 1,2,5-trimethyl-4-N-arylaminopiperidine derivatives, we synthesized substituted urethanes containing a 4-propyl(aUyl, propargyl)piperidine-4-yl fragment. To synthesize these compounds, we used 1,2,5-trimethyl-4-propyl(allyl, propargyl)-4-N-aryl(hetaryl)aminopiperidines, obtained by reacting 3'iminopiperidines (I) with the appropriate alkyl(alkenyl)magnesium halides. From N-(1,2,5-trimethylpiperidylidene-4)aniline and n-propyimagnesium bromide, 1,2,5-trimethyl-4-n-propyl-4-N-phenylaminopiperidine (II) was obtained with a yield of 25%. Reaction of the analogous imines with aUyimagnesium bromide proceeds well, with yields of the resulting aminopiperidines ranging from 50-95 %. Syntheses of 1,2,5-trimethyl-4-allyl-4-N-o-methoxyphenyl (III), [p-methoxyphenyl (IV), benzyl (V), 1phenylethyl (VI), 2-thiazolyl (VII), and 2-pyridylaminopiperidines (VIII)] have been described by us previously [3, 4, 7]. Similarly, from amines I, containing as the arylamine component o-(-p)methyl(bromo)-substituted aniline or m,p-dichloroaniline, we obtained 1,2,5-trimethyl-4-allyl-4-N-o-tollyl (IX), [p-tolyl (X), o-bromophenyl (XI), p-bromophenyl (XII), and m , p dichlorophenyl (XIII)] aminopiperidines.