2-(Methylamino)ethanol → 3-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-benzonitrile

Participants

Reaction Steps

To a solution of 2-(methylamino)ethanol (4 mL, 51 mmol) and TEA (4 mL, 28.05 mmol) in DCM (75 mL) under N2, was added 3-(bromomethyl)benzonitrile (5 g, 25.50 mmol) at 0° C. and the mixture was stirred at RT for 30 min. After this time, reaction mixture was concentrated under reduced pressure and the remaining residue was dissolved in DCM and washed with water to give the title compound as a colorless liquid (4.9 g, 100%). 1H NMR (DMSO-d6, 400 MHz) δ 7.76 (s, 1H), 7.69-7.71 (m, 2H), 7.63-7.65 (m, 1H), 7.49-7.53 (m, 1H), 4.41-4.43 (m, 1H), 3.47-3.51 (m, 2H), 3.32 (m, 2H), 2.40-2.43 (m, 2H), 2.13 (s, 3H).

Provenance & Evidence