3-Chlorobenzenesulphonyl chloride → HCID 58728405, compound

Participants

Reaction Steps

3-Chlorobenzenesulfonyl chloride (31.6 mg, 0.122 mmol) was added to a solution of 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 mmol) and diisopropyletheylamine (44.9 mg, 0.348 mmol) in DCM. The reactions were quenched with sat. NaHCO3 and separated with a hydrophobic frit. Flash chromatography on silica 0 to 10% MeOH in EtOAc afforded 1-[(1R,5S)-8-(2-{1-[(3-chlorophenyl)sulfonyl]-4-phenyl-4-piperidinyl}ethyl)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole 14.7 mg (20% yield). MS ES+ 603 (M+H). 1H NMR (300 MHz, chloroform-d) δ ppm 1.6 (m, 2H), 1.7 (m, 4H), 1.9 (m, 8H), 2.4 (m, 4H), 2.6 (s, 3H), 2.8 (m, 2H), 3.4 (m, 2H), 4.6 (m, 1H), 7.2 (m, 5H), 7.3 (m, 3H), 7.4 (t, J=7.9 Hz, 1H), 7.5 (m, 1H), 7.6 (d, J=7.8 Hz, 1H), 7.7 (m, 1H), 7.7 (m, J=1.8, 1.8 Hz, 1H).

Provenance & Evidence