N-Phenyl-p-phenylenediamine → 3-oxo-N-(4-phenylamino-phenyl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide

Participants

Reaction Conditions

Reaction Steps

HOBt (70 mg, 0.5 mmol) and DIEA (11 mg, 0.9 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (50 mg, 0.3 mmol) in DMF (3 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (80 mg, 0.5 mmol) followed by N-phenyl-benzene-1,4-diamine (100 mg, 0.3 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (10% methanol in chloroform) to afford 15 mg (10%) of 3-oxo-N-(4-phenylamino-phenyl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 511.19 (M+1)+, 96.55%, 1H NMR: (CDCl3): δ 7.7 (m, 1H), 7.6 (m, 2H), 7.4 (m, 4H), 7.1 (m, 1H), 7.0 (m, 3H), 6.8 (m, 1H), 4.0 (m, 2H), 3.8 (m, 2H), 3.4 (m, 3H), 3.2 (m, 2H).

Provenance & Evidence