1,1'-Carbonyldiimidazole → HCID 58728636, compound

Participants

Reaction Steps

To a solution of 1-cyanocyclopropane-carboxylic acid (38.9 mg, 0.351 mmole) in 1 ml of DCE was added carbonyldiimidazole (38.0 mg, 0.234 mmole) and the mixture was stirred until gas evolution stopped. 2-Methyl-1-{(1R,5S)-8-[2-(4-phenyl-4-piperidinyl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole (50.0 mg, 0.117 mmole) was added and the resulting mixture was stirred overnight. The solvent was evaporated and the reaction mixture was flashed on silica using a gradient of 1-8% MeOH in CHCl3 to afford 1-[(4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenyl-1-piperidinyl)carbonyl]cyclopropanecarbonitrile. MS ES+ 522 (M+H). 1H NMR (300 MHz, chloroform-d) δ ppm 1.6 (m, J=43.1 Hz, 6H), 1.9 (d, J=25.3 Hz, 10H), 2.4 (m, J=10.0 Hz, 4H), 2.6 (s, 3H), 3.3 (m, 3H), 3.5 (m, 1H), 4.1 (m, 2H), 4.7 (m, 1H), 7.3 (m, 8H), 7.7 (m, 1H).

Provenance & Evidence