Patent ID: 8952155
Filing Date: 2015-02-10
Classification: A61P,C07C,C07D

Abstract:
1. A process for the preparation of (E)-4-(2-cyanoethenyl)-2,6-dimethylphenylamine hydrochloride comprising (a) reacting 2,6-dimethyl-4-amino-l-carboxybenzyl phenyl amine with sodium nitrite in hydrochloric acid to form a diazotized compound, (b) reacting the diazotized compound with an alkali tetrafluoroborate to give the corresponding tetrafluoroborate salt, (c) reacting the tetrafluoroborate salt with acrylonitrile in presence of palladium acetate and a solvent to form 2,6-dimethyl-4-(2-cyanoethyl)-phenyl-1-carboxy benzylamine, (d) deprotecting the 2,6-dimethyl-4-(2-cyanoethyl)-phenyl-1-carboxy benzylamine with an acid, and (e) treating the product of step (d) with hydrochloric acid to afford (E)-4-(2-cyanoethenyl)-2,6-dimethylphenylamine hydrochloride, wherein the (E)-4-(2-cyanoethenyl)-2,6-dimethylphenylamine hydrochloride contains less than 0.5% of the Z-isomer.