Ethanol → 3-Methyl-3,8-diazabicyclo(3.2.1)octane

Participants

Reaction Steps

A solution of 8.2 g (0.038 mole) 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane in 80 ml absolute ethanol containing 0.11 mole dry hydrogen chloride was hydrogenated in the presence of 1.5 g 10% palladium on charcoal at ambient temperature and pressure for 20 hours. The precipitated hydrochloride salt of the desired product was dissolved by addition of a little water, and, after filtration, the solvent was removed carefully in vacuo. The crystalline residue (6.9 g) was triturated with ethanol-diethyl ether containing dry hydrogen chloride to insure complete formation of the somewhat unstable dihydrochloride salt. Filtration gave 6.0 g (79%) of pure product, melting point 272°-280° C (dec.) with sublimation above 200° C.

Provenance & Evidence