1,1'-Thiocarbonyldiimidazole → 1-(Acetyl)-4-(4-isothiocyanatophenyl)piperazine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-acetyl-4-(4-aminophenyl)piperazine (1.0 g; 4.6 mmol) (from Step B above) in N,N-dimethylformamide (10 mL) was added dropwise to a cooled (−15° C.) solution of thiocarbonyldiimidazole (855 mg, 4.8 mmol) in N,N-dimethylformamide (10 mL). After the addition was complete, the mixture was stirred at −15° C. for 30 min, then the cooling bath was removed and the solution was stirred for 1 h. Ice-water was added and the mixture was extracted with ether (4×50 mL). The combined ether layers were washed with brine, dried (MgSO4), filtered, and evaporated to give 1-(acetyl)-4-(4-isothiocyanatophenyl)piperazine (1.0 g, 84%).

Provenance & Evidence