Hydrochloric Acid → 8,9,10,11-Tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

Participants

Reaction Steps

Hydrogen chloride (300 mL of a 4 N solution in 1,4-dioxane) was added to a solution of tert-butyl 6-amino-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (34.74 g, 102.36 mmol) in dichloromethane (300 mL). The reaction was stirred overnight at ambient temperature and then concentrated under reduced pressure. The resulting solid was suspended in dichloromethane, isolated by filtration, and washed sequentially with dichloromethane, diethyl ether, hexane, and diethyl ether. The solid was then triturated with methanol and isolated by filtration to provide 11.58 g of 8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride as a white solid. The filtrate was concentrated under reduced pressure, dissolved in water, and precipitated with 1,4-dioxane to provide an additional 6.95 g of product.

Provenance & Evidence