1-Bromo-3-chloropropane → HCID 18995646, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.12 g, 2.56 mmole) in tetrahydrofuran (20 mL) was cooled to -78° C. Butyllithium (1.03 mL of 2.5M in hexanes, 2.56 mmole) was added and the reaction mixture was stirred for 5 minutes. 1-Bromo-3-chloropropane (2.7 mL, 25 mmole) was added and the reaction mixture was allowed to warm to ambient temperature. When the reaction was complete, as indicated by thin layer chromatography (silica gel, 30% ethyl acetate in hexanes v/v), the reaction mixture was diluted with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel eluting with 10-20% ethyl acetate in hexanes v/v) to provide 0.76 g of N,N-bis(phenylmethyl)-2-(4-chlorobutyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Provenance & Evidence