1,4-Dioxane → Ammonia

Participants

Reaction Steps

A mixture of 2,2,7,7-tetramethyl-[1,4]diazepane (1.1 g, 7.2 mmol) [Ramasseul, Rene; Rassat, Andre; Rey, Paul. Journal of the Chemical Society, Chemical Communications (1976), (3), 83-4], 5-bromo-2-chloroanisole (1.6 g, 7.2 mmol), potassium tertbutoxide (1.6 g, 14.5 mmol), palladacycle (200 mg, 0.21 mmol) and dioxane (20 ml) was stirred at reflux for 5 h. Water (50 ml) was added. The mixture was extracted with diethylether (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.50 g (23%). The hydrochloric acid salt was precipitated by stirring the free base in a mixture of concentrated hydrochloric acid (3.2 M) in diethylether. Mp 275-278° C.

Provenance & Evidence