Potassium Iodide → N-isopropyl-2-[2-(4-methoxybenzylamino)-phenylamino]-N-(4-methoxy phenyl)-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-methoxybenzyl)-benzene-1,2-diamine (2.42 g, 10.6 mmol) in DMF (40 mL) was added potassium carbonate (1.47 g,10.6 mmol), potassium iodide (176 mg, 1.06 mmol), and 2-Bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide acetamide (3.03 g, 10.6 mmol). The resultant reaction mixture was stirred overnight at 60° C. The solvent was removed in vacuo and the crude material dissoved in EtOAc (150 mL), washed with water (2×50 mL) and brine (50 mL), dried with MgSO4, filtered and concentrated to a brown oil. The precipitate which formed upon the addition of ether (70 mL) was filtered to give the title compound (1.39 g, 3.21 mmol) as a yellow solid. The remaining filtrate was concentrated under reduced pressure to a brown oil which was purified by flash chromatography on silica gel (40 g) eluted with EtOAc/Hexanes (1:4, 900 mL).

Provenance & Evidence