Potassium Carbonate → HCID 9889053, compound

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A mixture of N-(4-cyclohexyl-phenyl)-2-bromoacetamide (50 mg, 0.17 mmol), 4-(2-keto-1-benzimidazolinyl)-piperidine (41 mg, 0.18 mmol), and potassium carbonate (34 mg, 0.25 mmol) in dimethylsulfoxide (2 mL) was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated to give a yellow oil. The crude oil was purified on reverse phase silica gel column using 100% acetonitrile to give N-(4-cyclohexyl-phenyl)-2-[4-(2-oxo-2,3-dihydrobenzoimidazol-1-yl)-piperidin-1-yl]-acetamide as a yellow solid (21 mg, 30%): mp 130-132° C. 1H NMR (300 MHz, CDCl3) d 9.28 (s, 1H), 9.05 (s, 1H), 7.53 (d, 2H), 7.22 (d, 2H), 7.11 (m, 4H), 4.33 (m, 1H), 3.22 (s, 2H), 3.12 (d, 2H), 2.40 -2.60 (m, 5H), 1.70-1.90 (m, 7H), 1.20 -1.60 (m, 5H). MS m/z 433 (M+H+).

Provenance & Evidence