Triethylamine → HCID 58728519, compound

Participants

Reaction Steps

A mixture of 2-methyl-1-{8-[2-(4-phenyl piperidin-4-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole dihydrochloride (100 mg, 0.22 mmol), 2-benzofurancarboxylic acid (36 mg, 0.22 mmol) and triethylamine (66 mg, 0.66 mmol) in dimethylformamide (0.75 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (92 mg, 0.24 mmol) and the resulting mixture was stirred at rt for 1 h. The reaction mixture was diluted with water and the resulting precipitate was collected, washed with water and dried. The precipitate was purified by chromatography on silica gel eluting with 1:20 methanol:dichloromethane to give 1-((1R,5S)-8-{2-[1-(1-benzofuran-2-ylcarbonyl)-4-phenylpiperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole as a clear oil (0.075 g, 60%). 1H NMR (400 MHz, CDCl3) δ 7.66 (m, 2H), 7.52 (m, 1H), 7.26-7.44 (m, 9H), 7.16 (m, 2H), 4.61 (m, 1H), 4.16 (m, 2H), 3.40-3.57 (m, 2H), 3.26 (m, 1H), 2.57 (m, 3H), 2.34 (m, 4H), 1.94 (m, 9H), 1.62 (m, 4H). HRMS C37H40N4O2 m/z 573.3229 (M+H)Cal., 573.3238 (M+H)Obs..

Provenance & Evidence