Triethylamine → Ammonia

Participants

Reaction Steps

A suspension of 4-chloropyridine hydrochloride (7.5 g) in 3-methyl-1-butanol (100 ml) was added dropwise to a refluxing solution of hexahydro-1,4-diazepine (10.0 g) and triethylamine (16.8 ml) in 3-methyl-1-butanol (300 ml). After addition the solution was refluxed for 18 hours. The solvent was removed in vacuo to give an oil. Purification by sinter-column chromatography on silica gel, eluting with dichloromethane containing an increasing proportion of methanol (2-5%) and a small amount of conc. aqueous ammonia, gave 1-(4-pyridyl)hexahydro-1,4-diazepine as a colourless oil which slowly crystallised on standing.

Provenance & Evidence