Benzylamine → N-[(Trimethylsilyl)methyl]benzylamine

Participants

Reaction Steps

To a solution of chloromethyltrimethylsilane (1.34 kg, 10.96 mol) in acetonitrile (17.0 L) is added benzylamine (2.34 kg, 21.92 mol) and the reaction mixture is heated at reflux for 16 h. The reaction mixture is cooled to room temperature and the precipitate of benzylamine hydrochloride is removed by filtration. The filtrate is concentrated under vacuum to about 5 L and then diluted with water (5 L). The reaction mixture is extracted with hexane (2×5 L). The organic extracts are combined and washed with brine (5 L) and dried over MgSO4. The filtrate is concentrated under vacuum to give 1.77 kg (83%) of N-(trimethylsilylmethyl)benzylamine.

Provenance & Evidence