Hydrochloric Acid → 2-Piperidinepropanol
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.Cl>O.[Pt](=O)=O.O>[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-(3-Hydroxypropyl)pyridine (5 g, 36.44 mmoles) was dissolved in 1N HCl (36.4 mL, 36.4 mmoles) and water (63.6 mL) and platinum (IV) oxide monohydrate (1 g, 4.08 mmoles) was added under an argon atmosphere. The mixture was hydrogenated at 55 psi in a Parr bomb at 25° C. for 96 h. The catalyst was filtered off through Celite® and washed with water. The combined filtrates were treated with BioRad AG1-X8 (OH−) resin until basic. The resin was filtered off and washed with water. The combined filtrates were evaporated to dryness and the product was chromatographed on silica gel using 10% increasing to 20% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (5.22 g, 100%): CIMS: m/z 144.40 (MH+); δC (d6-DMSO) CH2: 24.0, 25.3, 28.8, 31.5, 32.8, 45.9, 60.8; CH: 56.1.