Acetic Acid → 6-Methoxy-8-{4-[1-(8-quinolinyl)-4-piperidinyl]-1-piperazinyl}quinoline

Participants

Reaction Steps

To a solution of 0.247 g of 6-methoxy-8-piperazino-quinoline (Step 4) in 10 mL of dichloroethane, was added 0.226 g of 1-quinolin-8-yl-piperidin-4-one (Step 6) followed by 0.274 g of sodium triacetoxyborohydride and 0.1 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water and dried over magnesium sulfate. The product crystallized and filtered to give 0.200 g of the desired product. Mp.194-197° C.; MS (ES) m/z (relative intensity): 454 (M++−H, 100).

Provenance & Evidence