Potassium Carbonate → 5-Chloro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1-methyl-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

33 mg of 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (0.18 mmol, 1.00 equiv), 58 mg of 5-chloro-1-methyl-1,3-dihydro-benzoimidazol-2-one (0.19 mmol, 1.05 equiv), 100 mg of K2CO3 (0.72 mmol, 4.0 equiv), and 0.8 mL of NMP were combined in a 4 mL vial. The resultant mixture was heated at 60° C. in an oil bath overnight. The crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent) to yield 5-chloro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1-methyl-1,3-dihydro-benzoimidazol-2-one (66): HPLC retention time=2.40 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.08% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected=449.0, found=449.1.

Provenance & Evidence