Methanol → (2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

4-Pyridinecarbaldehyde (5.36 g, 50 mmol) and 3-(2-aminoethyl)pyridine (6.5 ml, 50 mmol) were added to methanol (100 ml), and stirred at room temperature for 7 hours. The resulting mixture was cooled to 0° C. Sodium borohydride (2.8 g, 74 mmol) was added to the mixture, and stirred at 0° C. for 1 hour. Water was then added to the reaction mixture to distill the methanol off under reduced pressure. The residue was extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5→85:5). The purified product was concentrated under reduced pressure to thereby obtain 10.03 g (yield: 94%) of (2-pyridin-3-ylethyl)pyridin-4-ylmethylamine as a colorless oil.

1. temperatureThe resulting mixture was cooled to 0° C
2. stirringstirred at 0° C. for 1 hour
3. distillationto distill the methanol off under reduced pressure
4. extractionThe residue was extracted with dichloromethane
5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5→85:5)
9. concentrationThe purified product was concentrated under reduced pressure

ORD record

ord-ba57c84b555840709b8fb2744a8d8d38

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664217B2