1,2-Dimethoxyethane → Ammonia

Participants

Reaction Steps

A mixture of 9-methyl-3,9-diazabicyclo-[4.2.1]-nonane (1.50 g, 10.7 mmol), 3-chloro-5-ethoxypyridine (3.38 g, 21.4 mmol), potassium tert-butoxide (2.4 g, 21.4 mmol) and 1,2-dimethoxyethane (20 ml) was stirred at room temperature overnight. Aqueous sodium hydroxide (30 ml, 1 M) was added and the mixture was extracted two times with ethyl acetate (20 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 0.39 g, 21%. Mp. 142-144° C.

Provenance & Evidence