Acetone → HCID 67771606, compound

Participants

Reaction Steps

Sodium iodide (1 g, 6 mmole) and potassium carbonate (0.8 g, 6 mmole) were added to a solution of N,N-bis(phenylmethyl)-2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.55 g, 1.2 mmole) in acetone. The reaction mixture was heated at reflux for 4 hours, filtered, and then concentrated under vacuum. The residue was purified by flash chromatography (silica gel eluting with 10-15% ethyl acetate in hexanes v/v). Nuclear magnetic resonance spectroscopy indicated the possible presence of iodo intermediate; so the residue was taken up in acetone, combined with sodium iodide and potassium carbonate and heated at reflux over night. The reaction was worked up to provide 0.38 g of N,N-bis(phenylmethyl)-8,9,10,11 tetrahydropyrido-[1',2':1,2]imidazo[4,5-c]quinolin-4-amine.

Provenance & Evidence