Acetic Acid → 3-Piperidin-3-ylpropan-1-ol

A 500 mL Parr hydrogenation bottle was charged with 3-Pyridinepropanol (10.0 g, 72.9 mmol), platinum(IV)oxide hydrate (Adam's Catalyst) (500 mg), AcOH (30 mL), and HCl, 37% (1 mL). Contents of the bottle were hydrogenated at 47 psi for three days. EtOH and water were added, and the reaction mixture was filtered through CELITE. NaOH (10 N) was added and the mixture was extracted with methylene chloride, dried with anhydrous MgSO4, filtered and concentrated. The product was concentrated from PhMe and used without further purification. 1H NMR (CD3OD): δ 3.55 (t, J=5 Hz, 2H), 3.0{tilde over (5)} 2.95 (m, 2H), 2.5{tilde over (5)} 2.45 (m, 1H), 2.23 (t, J=10 Hz, 1H), 1.8 9 1.86 (m, 1H), 1.7{tilde over (0)} 1.66 (m, 1H), 1.6 0 1.44 (m, 4H), 1.2{tilde over (8)} 1.22 (m, 2H), 1.0 6 1.00 (m, 1H) ppm.

1. filtrationthe reaction mixture was filtered through CELITE
2. additionNaOH (10 N) was added
3. extractionthe mixture was extracted with methylene chloride
4. dry with materialdried with anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. concentrationThe product was concentrated from PhMe
8. customused without further purification

ORD record

ord-e4a8139c66f045edb010d4c57cc3fb25

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08591878B2