Sodium hydride → tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To 1.26 g (8.37 mmol) 4-chloro-benzoylcyanide was added bis-(2-chloroethyl)-carbamic acid tert-butyl ester (2.02 g, 8.37 mmol) in 25 ml N,N-dimethylformamide. The resulting mixture was stirred and cooled in an ice bath, then sodium hydride (60% suspension in mineral oil) (1.1 g, 42 mmol) was added portionwise. The reaction was brought to room temperature and then heated in an oil bath at 60° C. for 16 hours. The reaction mixture was quenched by addition of ice water and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed twice with water, once with brine, dried with magnesium sulfate and concentrated in vacuo. The residual brown oil was purified by silica gel chromatography eluting with hexane-ethyl:acetate (9:1) to give the title compound (1.44 g, 54%).

Provenance & Evidence