Diisopropylethylamine → 5-{4-[2-(3-Iodophenyl)ethyl]-1-piperazinyl)2-methylquinoline

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (1.7 mL; 1.5 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (1.31 g; 0.9 eq) and 2-(3-iodophenyl)ethyl methanesulfonate (2.1 g) in dimethylformamide (20 mL). The reaction mixture was heated to 90° C. for 5 hours. The dark solution was concentrated under reduced pressure, and purified by ion-exchange chromatography (SCX-2), eluting with methanol-ammonia/methanol (1M), (1:0) to (0:1). The combined basic fractions were concentrated under vacuum and purified by column chromatography (SPE cartridge, SiO2) using dichloromethane-methanol (95:5) to afford the title compound (1.5 g, 60% yield).

Provenance & Evidence