Tert-Butylamine → N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

Participants

Reaction Steps

To a solution of 5,5-diphenyl-2-cyclopenten-1-ol (0.20 g) in N,N-dimethylformamide (1 ml) were added methanesulfonyl chloride (0.35 ml) and triethylamine (0.60 ml) at 5° to 10° C. After being stirred for 1 hour, t-butylamine (1.78 ml) was added to the reaction mixture at 5° to 12° C. The reaction mixture was stirred for 3 days at room temperature. To the reaction mixture were added water and ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine (0.11 g).

Provenance & Evidence