p-Fluorophenethylamine → HCID 57166725, compound

Participants

Reaction Steps

A solution of 4.87 g (30 mmol) of carbonyldiimidazole and 3.43 g (30 mmol) of cyclohexylmethanol was stirred, under nitrogen and at room temperature, for 2-4 hours or the time until the TLC (silica gel; hexane-ethylacetate, 4:1) analysis indicated a complete disappearance of cyclohexylmethanol in the mixture. To this reaction mixture, a solution of 4-fluorophenylethyl amine (4.18 g, 30 mmol) in methylene chloride (5 mL) was added and stirred overnight. The TLC analysis indicated a complete disappearence of 4-fluorophenylethyl amine. The reaction mixture was extracted with 4×50 mL of methylene chloride. The combined extracts were washed with 5% HCl (2×50 mL), water, dried over MgSO4, and concentracted under vacuum. The solid was crystallized from hexane to furnish 5.0 g of N-(Cyclohexylmethyloxycarbonyl)-4-fluorophenylethyl amine (59% yield). mp 44°-45° C.

Provenance & Evidence