Dimethylformamide → {4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-(2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester

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Reaction Steps

Heat a solution of {4-[2-(4-methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-carbamic acid tert-butyl ester (200 mg, 0.38 mmol), 2-chloroethyl-1-piperidine hydrochloride (100 mg, 0.57 mmol) and 60% sodium hydride (38 mg, 0.94 mmol) in N,N-dimethylformamide to 60° C. and stir for 18 hours. Add potassium tert-butoxide (760 mg, 0.67 mmol) and 2-chloroethyl-1-piperidine hydrochloride (46 mg, 0.25 mmol) and stir for an additional 2 hours, then cool to ambient temperature. Dilute the reaction with dichloromethane, wash with saturated sodium bicarbonate, dry with magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures to give 120 mg of the title compound (50%). Mass spectrum (ion spray): m/z=631.3 (M+H).

Provenance & Evidence