N-Methylcyclohexylamine → 4-(bromomethyl)-N-cyclohexyl-N-methylbenzenesulfonamide

Participants

Reaction Steps

The 4-(bromomethyl)benzene-1-sulfonyl chloride (1 g, 3.71 mmol), Et3N (0.776 mL, 5.56 mmol) and N-methylcyclohexylamine (0.42 g, 3.71 mmol) were reacted overnight in THF (6 mL) at ambient temperature. The mixture was diluted with DCM and washed with water. The organics were dried over MgSO4, filtered, concentrated and purified by chromatography on silica gel using an heptane/EtOAc gradient (100/0 to 50/50) to give the title compound (0.317 g, 24.6%): 1H NMR (CDCl3) δ 7.88-7.77 (d, 2H, J=8.4 Hz), 7.52 (d, 2H, J=8.4 Hz), 4.62 (s, 2H), 3.87-3.60 (m, 1H), 2.75 (s, 3H), 1.79-1.69 (m, 2H), 1.66-1.57 (m, 1H), 1.52-1.50 (m, 1H), 1.30 (m, 4H), 1.14-0.84 (m, 2H)

Provenance & Evidence