4-Fluorobenzoyl chloride → HCID 11337818, compound

Participants

Reaction Conditions

Reaction Steps

Add 4-fluorobenzoyl chloride (155 mg, 0.976 mmol) to a solution of 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (preparation 2, 176 mg, 0.814 mmol) in pyridine (8 mL) and heat at 55° C. overnight. Remove the volatile under reduced pressure, dissolve the residue in DCM, wash with 0.1N NaOH, dry over sodium sulfate, filter and concentrate to give a residue. Purify the residue by chromatography (silica gel, 8% 2M NH3/MeOH in DCM) to provide the free base of the title compound (203 mg, 74%): MS (ES): m/z=339.2 (M+H)+; 1H NMR (CDCl3): δ 7.92 (m, 3H), 7.70 (s, 1H), 7.52 (d, 1H), 7.32 (t, 1H), 7.18 (m, 3H), 6.12 (m, 1H), 2.50 (m, 4H), 2.37 (s, 6H), 2.13 (m, 2H), 1.57 (m, 1H).

Provenance & Evidence