Benzyl chloroformate → HCID 53853329, compound

Participants

Reaction Steps

A solution of diisopropylethylamine (6.11 g), in dry tetrahydrofuran (20 ml) was added to a stirred solution of 5-cyano-1H-indole-3-ethanamine (7.3 g) in dry tetrahydrofuran (250 ml). A solution of benzyl chloroformate (7.73 g) in dry tetrahydroguran (20 ml) was then added at room temperature. After stirring for 1.5 h the reaction mixture was partitioned between water (100 ml). The aqueous layer was separated and extracted with ethyl acetate (4×50 ml). The combined organic solutions were washed with water (100 ml), dried (MgSO4) filtered and evaporated to afford an oily solid which was washed with petroleum spirit (b.p. 60°-80°, 100 ml) and then recrystallised from a mixture of ethyl acetate (50 ml) and petroleum spirit (b.p. 60°-80°, 35 ml) to afford the title compound (9.46 g), m.p. 127.5°-129°.

Provenance & Evidence