Dimethylformamide → HCID 18668741, compound

Participants

Reaction Steps

To a suspension of 1.20 g of 4-chloro-1-[2-(4-piperidyl)ethyl]-1H-imidazo-[4,5-c]quinoline trifluoroacetate and 0.77 g of potassium carbonate in 6 ml of N,N-dimethylformamide, 0.30 ml of n-butyl bromide was added dropwise at room temperature, and the mixture was stirred for 5 hours. The reaction mixture was adjusted to pH 10 with 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried, and then the solvent was evaporated to give 0.92 g of a pale brown liquid. The resulting liquid was dissolved in tetrahydrofuran. The solution was filtered on silica gel, and the filtrate was concentrated to give 0.87 g of a colorless solid. Hydrochloride was prepared in a conventional method. Recrystallization from a mixture of methanol and ethyl acetate gave colorless crystals having the melting point of from 144 to 158° C.

Provenance & Evidence