Acetyl chloride → Ondansetron

Participants

Reaction Steps

2.0 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one, 2 ml of N,N,N′,N′-tetramethyl- diaminomethane were suspended in 30 ml of toluene, and then 1.4 ml of acetyl chloride was slowly added thereto, which was then stirred for 10 min. 1.65 g of 2-methyl imidazole was added to the reaction mixture, which was then stirred under reflux for 10 hours. The reaction mixture was concentrated to remove the solvent, and then 150 ml dichloromethane and 50 ml of 1 N aq. sodium hydroxide were added to the resulting residue. The resulting organic layer was separated and dried over MgSO4, and then evaporated. The resulting solid was suspended in acetone, which was then stirred for 3 hours, and then filtered and dried to give 1.70 g of title compound (yield 58%).

Provenance & Evidence