2-Methylimidazole → Ondansetron

Participants

Reaction Steps

A solution of 3-(chloromethyl)-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one (0.50 g) and 2-methyl-1H-imidazole (1.60 g) in dry DMF was stirred under nitrogen at 90° for 3.75 h, and then poured onto water (25 ml). The suspension was stirred for 1 h, and the solid filtered off, washed with water (3×20 ml) and dried in vacuo at 50°. Column chromatography of this solid (0.53 g) eluting with a mixture of dichloromethane, ethanol and 0.88 aqueous ammonia (150:10:1) afforded the title compound (0.45 g) m.p. 228°-229°. This material was identical to the product from Example 7 by t.l.c. and n.m.r.

Provenance & Evidence