Triethylamine → N-(1-(4-(4-Fluorophenyl)phthalazin-1-yl)piperidin-4-yl)benzamide hydrochloride

Participants

Reaction Conditions

Reaction Steps

Combine 1-chloro-4-(4-fluorophenyl)phthalazine (150 mg, 0.58 mmol), N-(piperidin-4-yl)benzamide (178 mg, 0.87 mmol), triethylamine (0.404 mL, 2.9 mmol) and dimethylformamide (1 mL) at room temperature. Heat to 100° C. and stir overnight. Pour the crude reaction mixture onto a strong cation exchange Phenomenex Strata® SCX (55 μm, 70 Å) 10 g/60 mL column (with a benzene sulfonic acid functional group). Elute the desired product with 2 N methanolic ammonia (40 mL) and concentrate. Purify the residue by flash chromatography (20-30% [10% 2 N methanolic ammonia in ethyl acetate] in hexane). Add 1 N hydrochloric acid in diethyl ether to a solution of the isolated product in dichloromethane/methanol and remove the solvents under a stream of nitrogen gas to yield the title compound as a solid (137 mg, 51%). ES/MS m/z 427.2 (M+1).

Provenance & Evidence