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

Participants

Reaction Steps

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.

Provenance & Evidence