Sodium Bicarbonate → 8-{4-[2-(5-Methoxy-1-benzofuran-3-yl)-1-methylethyl)piperazin-1-yl]quinoline

Participants

Reaction Steps

To a stirred mixture of 1-(5-methoxy-1-benzofuran-3-yl)acetone (204 mg, 1 mmol) and 8-piperazino quinoline (213.0 mg, 1 mmol) in 1,2-dichloroethane (100 ml) and acetic acid (1 ml), sodium triacetoxyborohydride (422 mg, 2 mmol) was added at room temperature. Reaction mixture was stirred at room temperature for 72 hrs. At the end, reaction mixture was neutralized with 10% NaHCO3 and extracted with chloroform. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The product obtained was purified by silica-gel column chromatography by eluting it initially with 80% ethyl acetate:hexane and then with 5% methanol:ethyl acetate, yielding a brown semi-solid. Yield: 60 mg (14%); (M+H): 402; 1HNMR (400 MHz, CDCl3): δ 8.90˜8.88 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 8.13˜8.10 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 7.60˜6.70 (m, 8H); 3.87 (s, 3H); 3.50˜2.50 (m, 11H); 1.15˜1.13 (d, J=6.0 Hz, 3H).

Provenance & Evidence