N,N,N',N'-Tetramethylmethanediamine → Zofran

Participants

Reaction Conditions

Reaction Steps

2.0 g of 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one, 1.65 g of 2-methyl imidazole and 2 ml of N,N,N′,N′-tetramethyldiaminomethane were suspended in 5 ml of acetonitrile and 30 ml of toluene, and then 4 ml of chlorotrimethylsilane was slowly added thereto. The reaction mixture was stirred under reflux for 10 hours. The reaction mixture was concentrated to remove the solvent, and then 50 ml of water was added to the resulting residue. The resulting solid was filtered and dried, which was then suspended in acetone and stirred for 3 hours. The resulting solid was filtered and dried under a reduced pressure, which was then suspended in acetone, and then HCl was slowly added to thereto. The resulting suspension was stirred for 3 hours and cooled at 10° C. and below, which was then additionally stirred for 1 hour. The resulting solid was filtered and washed with acetone. The resulting solid was suspended in dichloromethane, which was then stirred under reflux for 1 hour and cooled at room temperature. The resulting solid was filtered and recrystallized with 10% aq. isopropyl alcohol to give 1.94 g of title compound (yield 53%).

Provenance & Evidence