Methane → Pirtenidine hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-octylaminopyridine (25 g., 0.121 mole) and octyl chloride (20.5 ml., 0.121 mole) was heated at 180° C. for 1 hr. More octyl chloride (0.5 ml.) was added and the mixture was again heated at 180° C. for 1 hr., then dissolved in dichloromethane. The dichloromethane solution was treated with charcoal, filtered, and stripped of solvent under vacuum. The solid residue was slurried in ether (1.5 kg.), collected by filtration, washed with ether (500 g.), isolated in a dry bag, and dried (50°-80° C., 0.1 mm.). The procedure was repeated using the same amounts of starting materials and the products were combined, affording N-(1-octyl-4(1H)-pyridinylidene)octanamine monohydrochloride (80.5 g., 93% yield, m.r. 120°-125° C.), which is the monohydrochloride salt of the compound of Formula I wherein R and R' are both octyl.

Provenance & Evidence