Dimethylformamide → 4-[4-(3-Indolyl)piperidinomethyl]-2-propionylaminothiazole

Participants

Reaction Steps

To a mixture of 4-[4-(3-indolyl)piperidinomethyl]-2-aminothiazole (1.5 g), triethylamine (2.68 ml) and N,N-dimethylformamide (15 ml) was added dropwise a solution of propionyl chloride (0.63 ml) in methylene chloride (1.2 ml) over a period of 10 minutes under ice-cooling and the mixture was stirred for 4.5 hours. The reaction mixture was dissolved in a mixture of chloroform and methanol (100 ml, 10:1 V/V) and the solution was washed with water (50 ml×3) and brine (50 ml) successively, and dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to column chromatography on silica gel and the column was eluted with a mixture of chloroform and methanol (30:1 to 15:1 V/V). The fractions containing the desired compound were combined and concentrated to give a residue, which was recrystallized from ethanol to give 4-[4-(3-indolyl)piperidinomethyl]-2-propionylaminothiazole (0.72 g).

Provenance & Evidence