Furfuryl Alcohol → N,N-diethyl-4-[[4-(2-furanylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of furfurylalcohol (0.19 ml; 2.24 mmol) and triethylamine (0.52 ml; 3.73 mmol) in methylene chloride (4 ml) was added methanesulfonyl chloride (0.17 ml; 2.24 mmol). The mixture was stirred 1 hour at 0° C., then compound 1 (300 mg; 0.75 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight, then heated to 45° C. and stirred for 1½ hours. The reaction mixture was allowed to cool to room temperature and NaOH 2N was added untill pH was basic. The mixture was extracted with methylene chloride (3×). The combined methylene chloride extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by reverse phase using 10%-25% CH3CN/H2O (TFA as the buffer) gave 197 mg of desired product (TFA salt).

Provenance & Evidence