Synthesis of new amides of the N-methylpiperazine series
New carboxylic acid amides containing an N-methylpiperazine fragment were synthesized by reactions of 1-methylpiperazine or 3- and 4-(4-methylpiperazin-1- ylmethyl)aniline with 4-chlorobenzoyl chloride and of 4-methyl-3-nitroaniline with 4-(4-methylpiperazin-1-ylmethyl)benzoyl chloride or benzotriazol-1-yl 4-(4-methylpiperazin-1-ylmethyl)benzoate. 4-Chloro-N-[4-(4-methylpiperazin-1- ylmethyl)phenyl]benzamide reacted with imidazole, quinolin-5-amine, and 2-methylquinolin-5-amine to give substituted 4-amino-N-[4-(4- methylpiperazin-1-ylmethyl)phenyl]benzamides. 4-Methyl-3-nitrophenyl-4- methylpiperazin-1-yl-substituted benzamides were reduced with hydrazine hydrate over Raney nickel to obtain N-(3-amino-4-methylphenyl)-4- (4-methylpiperazin-1- ylmethyl)benzamide as key intermediate in the synthesis of antileukemic agent imatinib and its isomer with alternative position of the amide group, 4-[(3-amino-4-methylphenylamino)methyl]phenyl- (4-methylpiperazin-1-yl)} methanone. Pleiades Publishing, Ltd., 2011.
Koroleva,Gusak,Ignatovich,Ermolinskaya
p. 1556 - 1563
(2012/03/09)
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