Ethanol → HCID 20562683, compound

Participants

Reaction Steps

Xanthine (30.4 g) was dissolved in aqueous sodium hydroxide solution (8 g in 500 ml) containing ethanol (100 ml). The solution was stirred, and diethylaminoethyl chloride (liberated from its salts) (27.0 g) was added at room temperature. The mixture was stirred on a steam bath for 18 hours, then evaporated to dryness. The residue was fractionally recrystallised from isopropyl alcohol to give 7-(2-diethylaminoethyl)xanthine (7.5 g). The solid was stirred in dry tetrahydrofuran (1 liter) at -15° C. under nitrogen. Butyl lithium (90 ml) was then added by syringe, and the mixture was stirred for 2 hours. Methyl iodide (12.8 g) was then added and the mixture was stirred and allowed to warm to room temperature. It was then stirred overnight, quenched with water and extracted with chloroform. The extracts were then washed, dried, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in ethanol and treated with ethanolic hydrogen chloride, then evaporated to dryness. The residue was recrystallised from isopropyl alcohol to give 8-methyl-7-(2-diethylaminoethyl)theophylline hydrochloride (3.1 g), mp 230°-232° C.

Provenance & Evidence