Cyclohexene → 3-((Pyridin-2-yl)amino)propan-1-ol

A mixture of 2-(3-hydroxypropyl)aminopyridine N-oxide (3.0 g, 17.9 mmol), as prepared in the preceding step, cyclohexene (10 ML, 100 mmol), and 10% palladium(0) on carbon (300 mg) in ethanol (50 mL) was heated to reflux. After two days, the reaction mixture was cooled. The catalyst was removed by filtration through Celite and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 5% methanol in methylene chloride) to give the title compound as a colorless oil (2.4 g, 88%). 1H-NMR (400 MHz, CDCl3) δ 8.02 (d, J=5.0 Hz, 1H), 7.37 (t, J=7.8 Hz, 1H), 6.54 (d, J=6.0 Hz, 1H), 6.39 (t, J=8.0 Hz, 1H), 4.69 (br s, 2H), 3.65 (t, J=5.5 Hz, 2H), 3.53 (q, J=5.9 Hz, 2H), 1.77 (t, J=5.6 Hz, 2H).

1. temperaturewas heated to reflux
2. temperaturethe reaction mixture was cooled
3. customThe catalyst was removed by filtration through Celite
4. concentrationthe filtrate was concentrated
5. customThe residue was purified by flash column chromatography (silica gel, 5% methanol in methylene chloride)

ORD record

ord-9ed827286b3c45f187f04928fc0e6949

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241789B2