Hydrochloric Acid → 2-(5-Methylpyridin-2-yl)ethanamine dihydrochloride

Temperature

60 °C

To a solution of 18 g of crude 2-(5-methylpyridin-2-yl)acetonitrile in dry THF (100 mL) was added dropwise Borane-tetrahydrofuran complex (1.0 M in THF, 232 mL, 232.5 mmol, 4 eq) at 0° C. under N2 atmosphere. The reaction mixture was then heated to 60° C. overnight. The reaction was cooled to room temperature, aq.HCl (6 N, 40 mL) was added carefully and the reaction mixture was then heated at 70° C. for 2 hrs. After cooling, water was added and the resulting solution was washed with ether. The aqueous layer was basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3 then extracted with ether (5×100 mL). The organic layer was dried over MgSO4, filtered and evaporated to give 7.6 g of crude 2-(5-methylpyridin-2-yl)ethanamine. (96% crude yield)

1. temperatureThe reaction was cooled to room temperature
2. temperaturethe reaction mixture was then heated at 70° C. for 2 hrs
3. temperatureAfter cooling
4. washthe resulting solution was washed with ether
5. customwas basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3
6. extractionthen extracted with ether (5×100 mL)
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. customevaporated

ORD record

ord-59b4f69bc4324fc8af9708de1ed54211

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318947B2