1-Benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridine → 3-(Piperidin-4-yl)pyridine

Reaction equation

C(OC([N:11]1[CH:16]=[CH:15][CH:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[CH:18]=1

Participants

Procedure

A solution of 1-benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridine (0.714 in ethanol (50 mL) was treated with 10% palladium on carbon (0.1 g) and hydrogenated under a hydrogen atmosphere at room temperature and 3.44 bar for 16 hours. The reaction mixture was filtered through diatomaceous earth to remove the catalyst, and the resulting filtrate was evaporated to afford the piperidine (0.393 g); NMR (CDCl3): 1.7 (m, 4), 2.8 (m, 4), 3.2 (m, 2), 7.3 (m, 1), 7.5 (m, 1), 8.5 (m, 2); MS: m/z=162(M+1).