Potassium Iodide → HCID 12919832, compound

Participants

Reaction Steps

A mixture of 1-(3-chloropropyl)isatin (13.44 g), 1-benzhydrylpiperazine (19.92 g), triethylamine (7.2 g) and potassium iodide (9.96 g) in N,N-dimethylformamide (144 ml) was stirred for 1.5 hours at 80° to 85° C. The reaction mixture was cooled, poured into a cold aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated. The residue was dissolved in chloroform and subjected to column chromatography on silica gel (60 g) using chloroform as an eluent. The eluate was evaporated, and the remaining oil was dissolved in ethanol (160 ml). To a solution was added 29% ethanolic hydrogen chloride (30 ml) under cooling or an ice bath, and the resultant mixture was stirred for 10 minutes. The precipirated crystals were collected by filtration and then dried to give 1-[3-(4-benzhydryl-1-piperazinyl)propyl]isatin dihydrochloride (20.17 g). Thus obtained product was purified by recrystallization from 92% ethanol (410 ml) to give the purified product of the same compound (10.44 g), mp. 245° to 248° C. (dec.).

Provenance & Evidence