1-Methylpiperazine → 2-(4-N-Methylpiperazino)-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan

Participants

Reaction Steps

To a stirred solution of 2-bromo-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan (20 mg, 0.047 mmol) in a mixture of acetonitrile/dichloromethane; 1:1 (2 mL) was added N-methylpiperazine (50 μL, excess) and the reaction mixture was stirred at room temperature for 1 hour. After this time the solvent was removed by distillation under vacuum and the product was purified by PTLC (eluent=hexane/ethyl acetate; 4:6+1% triethylamine) to give the title compound as a green yellow paste which was crystallized by freeze drying in t-butanol to give a yellow solid; (8 mg, 43%); 1H NMR (300 MHz, CDCl3) δ 7.07 (s, 2H, benzoyl Hs), 6.93 (d, 1H, J=8.60 Hz), 6.84 (d, 1H, J=2.25 Hz), 6.65 (dd, 1H, J=8.64, 2.30 Hz), 3.92 (s, 3H, OMe), 3.83 (s, 6H, 2×OMe), 3.78 (s, 3H, OMe), 3.66-3.64 (bm, 4H), 2.65-2.63 (bm, 4H), 2.40 (s, 3H, N-Me); 13C NMR (75 MHz, CDCl3) δ 188.76 (CO), 162.24, 155.88, 152.72, 149.06, 141.09, 135.36, 121.68, 119.64, 110.42, 106.11, 155.88, 95.63, 60.64, 55.88, 55.44, 53.88, 47.06, 45.29.

Provenance & Evidence