2-Bromopyridine → HCID 20041079, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromopyridine (4.8 g) in dry ether (30 ml) was added to a 1.7M solution of butyllithium in hexane (18 ml) at -78° C. with stirring. After one hour at that temperature a solution of 1-(4-biphenylyl)cyclobutanecarbonitrile (4 g) in a mixture of dry ether (80 ml) and dry tetrahydrofuran (10 ml) was added and the temperature allowed to rise to 0° C. After cooling to -20° C., methanol (20 ml) and then water (30 ml) were added dropwise. The aqueous mixture was extracted with ether and the ether extract washed, dried and evaporated to give [1-(4-biphenylyl)cyclobutyl](pyrid-2-yl)methanimine as an orange oil. The oil was dissolved in propan-2-ol (200 ml) and heated under reflux with sodium borohydride (2.0 g) for five hours. Water was added and the propan-2-ol removed by evaporation. The aqueous residue was extracted with ether. Hydrogen chloride gas was passed into the dried ether extract to give a gum which was heated with propan-2-ol to give a white solid which was recrystallised from a mixture of methanol and propan-2-ol to give [1-(4-biphenylyl)cyclobutyl](pyrid-2-yl)methylamine dihydrochloride hydrate (m.p. 240° C. (dec)).

Provenance & Evidence