Ethanolamine → 2-(2-Aminoethoxy)pyridine

A mixture of 500 mg of 2-aminoethanol and 328 mg of 60% sodium hydride-mineral oil dispersion in dioxane (27 mL) was heated to reflux for 30 min. After cooling to room temperature, 930 mg of 2-chloropyridine was added and the mixture was warmed to reflux and maintained at this temperature for 18 hrs. The reaction mixture was concentrated, diluted with water, and extracted with chloroform (3×). The organic extracts were washed with saturated brine, dried over sodium sulfate, filtered, concentrated, and the residue was purified by silica gel chromatography to give the title product as a yellow oily material. MS (M+H)+=138.9.

1. temperaturewas heated
2. temperatureto reflux for 30 min
3. temperaturethe mixture was warmed
4. temperatureto reflux
5. temperaturemaintained at this temperature for 18 hrs
6. concentrationThe reaction mixture was concentrated
7. additiondiluted with water
8. extractionextracted with chloroform (3×)
9. washThe organic extracts were washed with saturated brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customthe residue was purified by silica gel chromatography

ORD record

ord-8ac44687f63a4fd490a9183189096c5e

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709473B2