Methanol → 1-(Pyridin-3-yl)ethan-1-amine

3-Acetylpyridine (2.4 g, 20 mmol, Aldrich) was dissolved in 2M ammonia solution in methyl alcohol (50 mL, 100 mmol, Aldrich) and acetic acid (15 mL, J. T. Baker) was slowly added at 0 C. After stirring for 3 h at room temperature, the sodium cyanoborohydride (5.0 g, 80 mmol, Aldrich) was added to the solution at 0 C. The mixture was stirred under nitrogen at room temperature for overnight then the reaction was cooled at ice bath and quenched with aqueous 5 N sodium hydroxide (30 mL, 150 mmol, J. T. Baker). The methyl alcohol was removed from the mixture via vacuo. The residue was extracted by diethyl ether (30 mL×4). The combined organic phases were dried over anhydrous magnesium sulfate and concentrated via vacuo to give crude 1-pyridin-3-yl-ethylamine as light yellow oil in 44% yield (1.07 g, 8.8 mmol).

1. stirringThe mixture was stirred under nitrogen at room temperature for overnight
2. temperaturethe reaction was cooled at ice bath
3. customThe methyl alcohol was removed from the mixture via vacuo
4. extractionThe residue was extracted by diethyl ether (30 mL×4)
5. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
6. concentrationconcentrated via vacuo

ORD record

ord-a0e675e6f6964a7b9abf56cee18930a1

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524873B2