Methylamine → Methyl[2-(pyridin-4-yl)ethyl]amine

Ethyl-4-pyridylacetate (2 g) was allowed to stand in methanol (50 ml), saturated with methylamine gas, for 3 days. The solution was evaporated under reduced pressure and the residue heated under reflux for 16 hours in toluene (20 ml) with boranedimethylsulphide complex (1.26 ml). The solution was cooled then treated with methanol (1.5 ml) for 1 hour. Hydrogen chloride gas was bubbled through the solution until the pH was less than 2. The solution was heated under reflux for 1 hour then cooled and concentrated. Aqueous sodium hydroxide was added and the mixture extracted with ethyl acetate. The ethyl acetate solution was dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a yellow oil.

1. customThe solution was evaporated under reduced pressure
2. temperaturethe residue heated
3. temperatureunder reflux for 16 hours in toluene (20 ml) with boranedimethylsulphide complex (1.26 ml)
4. temperatureThe solution was cooled
5. additionthen treated with methanol (1.5 ml) for 1 hour
6. customHydrogen chloride gas was bubbled through the solution until the pH was less than 2
7. temperatureThe solution was heated
8. temperatureunder reflux for 1 hour
9. temperaturethen cooled
10. concentrationconcentrated
11. additionAqueous sodium hydroxide was added
12. extractionthe mixture extracted with ethyl acetate
13. dry with materialThe ethyl acetate solution was dried (Na2SO4)
14. customevaporated under reduced pressure

ORD record

ord-f7e2153dd8b444548c47569d30281c41

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05554627