Sodium Iodide → Acetonitrile, [(1,1-dimethylethyl)(phenylmethyl)amino]-

Participants

Reaction Steps

Benzyl(tert-butyl)amine (10.0 g, 61.3 mmol) was dissolved in acetonitrile (100 ml), and bromoacetonitrile (4.5 ml, 64.6 mmol), potassium carbonate (16.9 g, 122.3 mmol) and sodium iodide (9.2 g, 61.4 mmol) were successively added with stirring at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was diluted with saturated aqueous potassium carbonate solution, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure, and the obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (10.8 g, yield 87%) as a pale-yellow oil.

Provenance & Evidence