1,4-dibenzylpiperidin-4-ol → 4-Benzyl-4-piperidinol

HRID 1901085Notes

Reaction equation

HRID 1901085 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:15]([C:11]1([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 47141251,4-dibenzylpiperidin-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 981524-Benzyl-4-piperidinol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyl-4-benzyl-4-piperidinol (2.0 g, 7.1 mmol) and 10% palladium on charcoal catalyst (0.5 g) in absolute ethanol (100 ml), was stirred vigorously at 40° C. under a balloon of hydrogen for 5 h. The reaction mixture was then filtered through a pad of Celite and the filtrate concentrated in vacuo to a grayish solid. This material was dissolved in methanol and filtered a second time through Celite and the filtrate concentrated in vacuo to the product, a white solid.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite
  2. concentrationthe filtrate concentrated in vacuo to a grayish solid
  3. dissolutionThis material was dissolved in methanol
  4. filtrationfiltered a second time through Celite
  5. concentrationthe filtrate concentrated in vacuo to the product

Sources & evidence

ORD record
ord-b57c6caebf254421a1e6d52301a68676
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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