Hydrochloric Acid → Bis(2-pyridyl)methylamine

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.

1. temperaturethe resulting solution heated
2. temperatureat reflux for 5 hours
3. temperatureThe reaction mixture was then cooled in an ice bath
4. customSolvent was removed under reduced pressure
5. dissolutionthe residue dissolved in water (30 ml)
6. washwashed with ether (3×10 ml)
7. extractionThe solution was then extracted with dichloromethane (3×20 ml)
8. dry with materialthe combined organic phase dried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated to a brown oil (1.6 g, 86%)

ORD record

ord-54295c47e8df4f718e56100cb405045e

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05908851