Dimethylformamide → Ammonia

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-bromo-5-chloro-3-pyridyl)-4-tert-butoxycarbonyl-piperazine (2.0 g, 5.3 mmol), tetramethyltin (1.9 g, 10.6 mmol), palladium-di-(triphenylphosphine (0.19 g, 0.26 mmol) and dimethylformamide (2 ml) was stirred at 160° C. in a sealed vessel overnight. The mixture was stirred in conc. hydrochloric acid (30 ml) at reflux for 15 min. The mixture was evaporated. Aqueous sodium hydroxide (50 ml, 1 M) was added and the mixture was extracted with dichloromethane (3×50 ml). Chromatography of this crude mixture on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 0.70 g (43%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp 178.1-180.5° C.

Provenance & Evidence