Hydrochloric Acid → Bis(2-pyridyl)methylamine

Participants

Reaction Steps

To a solution of di-2-pyridyl ketone (1.84 g, 10 mmol) and ammonium acetate (7.7 g, 100 mmol) in anhydrous methanol (30 ml) was added sodium cyanoborohydride (1.26 g, 20 mmol) and the resulting solution heated at reflux for 5 hours. The reaction mixture was then cooled in an ice bath and acidified to pH 2 with concentrated HCl. Solvent was removed under reduced pressure and the residue dissolved in water (30 ml), washed with ether (3×10 ml) then basified to pH 10 with solid sodium hydroxide. The solution was then extracted with dichloromethane (3×20 ml) and the combined organic phase dried over anhydrous MgSO4, filtered and concentrated to a brown oil (1.6 g, 86%). The crude product was used directly in the next step.

Provenance & Evidence