Ethyl Acetate → 4-(p-Tolyl)piperidin-4-ol

HRID 1448977Notes

Reaction equation

HRID 1448977 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([OH:21])([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[H][H]>[Pd].C(O)C>[OH:21][C:11]1([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 1986081-Benzyl-4-(4-methylphenyl)piperidin-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 939124-(p-Tolyl)piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

30 g of N-benzyl-4-hydroxy-4-(4-methylphenyl)-piperidine in a mixture of equal parts of ethyl acetate and ethanol with palladium (5% on charcoal) is hydrogenated until one equivalent of hydrogen has been absorbed to give 4-hydroxy-4-(4-methylphenyl)-piperidine, m.p. 137°-138° (from ethyl acetate).

Workup

  1. customhas been absorbed

Sources & evidence

ORD record
ord-837cd625f1cc428287521841d5bcbe66
Source dataset
uspto-grants-1980_02
Patent number
US04188396

Reaction notes

Loading…