1,1'-Carbonyldiimidazole → 2,3,4,9-Tetrahydro-1h-carbazole-6-carboxamide

Participants

Reaction Steps

A mixture of 1,2,3,4-tetrahyrocarbazole-6-carboxylic acid (100 mg, 0.46 mmol) and 1,1′-carbonyldiimidazole (78 mg, 0.48 mmol) in 5 mL of anhydrous tetrahydrofliran was stirred for 8 hours. A solution of 4-[4-(2,3-dichlorophenyl)piperazin-1-yl]-1-aminobutane (140 mg, 0.46 mmol) in 1 mL of tetrahydrofuran was added and the resulting mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with aqueous Na2CO3 solution, dried (Na2SO4) and concentrated in vacuo to afford the free base of the title compound, N-(1-{4-[4-2,3-dichlorophenyl)piperazin-1-yl]}butyl)-1,2,3,4-tetrahydrocarbazole-6carboxamide, (161 mg, 70%). The hydrochloride salt was prepared by treating the free base with a solution of hydrogen chloride in ethyl acetate (mp 236-238° C.).

Provenance & Evidence