4-Aminobenzoic Acid → (4-Aminophenyl)(4-phenylpiperazin-1-yl)methanone

Participants

Reaction Steps

To a stirred suspension of 4-aminobenzoic acid (5 g, 36.5 mmol) in acetonitrile (100 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (7.67 g, 40.2 mmol), hydroxybenzotriazole hydrate (0.49 g, 3.65 mmol), 1-phenylpiperazine (11.2 ml, 3.65 mmol) followed by triethylamine (12.8 ml, 91.3 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction was diluted with the addition of water and the resulting aqueous mixture extracted using dichloromethane (3×100 ml). The organics were combined, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by flash column chromatography (SiO2) eluting with ethylacetate/dichloromethane (1:1) to afford the title compound as an off white solid. HPLC retention time 7.1 min. Mass spectrum (ES+) m/z 282 (M+H).

Provenance & Evidence