Imidazole → 4-Chloro-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenylpropyl]amino]benzonitrile

Participants

Reaction Steps

A solution of 4-chloro-2-[(3-hydroxy-1-phenylpropyl)amino]benzonitrile (2.3 g, 8 mmol) in dry tetrahydrofuran (50 ml) was treated with tert-butyldimethylsilylchloride (2.41 g, 2 eq.) and imidazole (1.09 g, 2 eq.) and stirred at room temperature for 1 h. The reaction mixture was diluted with water (200 ml) and the products extracted into diethyl ether (200 ml). The organic extract was dried over magnesium sulphate and concentrated to an oil. The crude product was purified on silica gel eluting with isohexane/diethyl ether (2:1) to afford the title compound as a colourless oil (2.3 g, 72%).

Provenance & Evidence