4-Fluorobenzoyl chloride → N-(3-(4-Dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-4-fluoro-benzamide hydrochloride salt

Participants

Reaction Steps

Reflux a mixture of 3-(4-dimethylamino-cyclohex-1-enyl)-2-fluoro-phenylamine (preparation 8, 0.115 g, 0.49 mmol) and 4-fluoro-benzoyl chloride (93 mg, 0.586 mmol) in dioxane (20 mL) for 2 hrs. Filter the reaction mixture through a SCX column (Bond Elut™, 10 g), wash with MeOH, elute the product with 2M NH3 in MeOH, evaporate the solvent, and further purify on a silica gel column (DCM:2M NH3 in MeOH, gradient) to give the free base of the title compound (0.125 g, 72%): MS (ES): m/z=357 (M+H)+. 1H NMR (CDCl3): δ 8.30 (m, 1H), 8.00 (m, 1H), 7.91 (m, 2H), 7.18 (m, 2H), 7.12 (m, 1H), 6.99 (m, 1H), 5.90 (m, 1H), 2.68 (m, 1H), 2.50 (m, 3H), 2.43 (s, 6H), 2.26 (m, 1H), 2.15 (m, 1H), 1.64 (m, 1H).

Provenance & Evidence