2-Chloro-4-fluorobenzoyl chloride → HCID 69350991, compound

Participants

Reaction Steps

Combine chiral 3-(4-dimethylamino-cyclohex-1-enyl)-5-fluoro-phenylamine (isomer 5A, preparation 5, 0.25 g, 1.07 mmol), 2-chloro-4-fluoro-benzoyl chloride (0.31 g, 1.6 mmol) and 1,4-dioxane (5 mL) and heat to reflux for 3 hr. Cool to ambient temperature and remove volatiles. Purify the residue by flash chromatography (silica gel, 10% 2M NH3/MeOH in DCM) to obtain the free base of the title compound (0.34 g, 81%). Convert to the hydrochloride salt by dissolving in ether and treating with 1M HCl in ether: MS (ES) m/z=391 (M+H)+; 1H NMR of free base (CDCl3): δ 8.19 (s, 1H), 7.72 (m, 1H), 7.42 (d, 1H, J=10 Hz), 7.26 (s, 1H), 7.16 (m, 1H), 7.06 (m, 1H), 6.86 (d, 1H, J=10 Hz), 6.09 (bs, 1H), 2.40 (m, 4H), 2.32 (s, 6H), 2.11 (m, 2H), 1.53 (m, 1H).

Provenance & Evidence