4-Chloro-1,2-diaminobenzene → 5-(5-Chlorobenzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

Participants

Reaction Conditions

Reaction Steps

A solution of 5-formyl-3-(1-methylpiperidin-4-yl)-1H-indole (0.210 g, 0.90 mmol), and 4-chloro-o-phenylenediamine (0.197 g, 1.38 mmol), in 15 mL of nitrobenzene was heated, with stirring, at 150-160° C. for 24 hours. The solution was allowed to cool to room temperature, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography (dichloromethane:methanol 10:1.5) to give the title compound (0.215 g, 68%) as an amorphous tan solid. FDMS m/e=365 (M+). EA calculated for C21H21N4Cl.¼ H2O C, 68.28; H, 5.87; N, 15.17. Found: C, 68.32; H, 6.17; N, 14.51.

Provenance & Evidence