To a stirring solution of 4-(ethylsulfonyl)benzonitrile (1.0 g, 5.12 mmol) in methanol (30 mL) was sequentially added nickel ruanne (500 mg) and ammonia (2.0 mL) at room temperature. The reaction mixture was transferred to a Parr reactor and hydrogenated at 60 psi hydrogen pressure for 1 hour. Upon completion of the reaction, the mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography. Subsequently, the purified free base was reacted with ethyl acetate solution of hydrochloric acid with stirring to give 513 mg of the target product [4-(ethylsulfonyl)phenyl]methylamine hydrochloride. The product characterization data were as follows: nMR (300 MHz, DMSO-d6) δ 1.09 (t, J = 7.5 Hz, 3H), 3.32 (q, J = 7.5 Hz, 2H), 4.15 (s, 2H), 7.76 (d, J = 7.2 Hz, 2H), 7.93 (d, J = 8.4 Hz, 2H), 8.50 (br s, 2H). ESI-MS (m/z) 200 ([M + H]+).
