39191-07-6

104-83-6

74-89-5

39191-07-6

GENERAL STEPS: An ethanol solution of methylamine (33% w/v, 17 mL) was slowly added dropwise to 4-chlorobenzyl chloride (2.0 g, 12.42 mmol), followed by heating the reaction mixture to reflux overnight. Upon completion of the reaction, ethanol was removed by distillation under reduced pressure by rotary evaporator. The residue was diluted with deionized water (100 mL) and washed with ethyl acetate (150 mL × 2). The aqueous phase was adjusted to pH 8 with solid potassium carbonate and then extracted with ethyl acetate (100 mL × 2). All organic phases were combined, washed with deionized water (100 mL), dried over anhydrous sodium sulfate, and finally the target product, N-methyl-3-chlorobenzylamine (1.7 g), was obtained by concentration under reduced pressure. The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 2.22 (s, 3H), 3.32 (br s, 1H), 3.62 (s, 2H), 7.25-7.38 (m, 4H); ESI-MS (m/z) 156 (M + H).