1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-4-(3-phenylpropyl)-4-piperidinol

HRID 26070Notes

Reaction equation

HRID 26070 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:14])[CH:10]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:38])([CH3:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][C:25]=2[O:39]CC2C=CC=CC=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:38][C:30]([C:27]1[CH:28]=[CH:29][C:24]([CH:10]2[C:11]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]2)=[C:25]([OH:39])[CH:26]=1)([CH3:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 2

HCID 204997841-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinolHCID 178418361HCID 178418361, compound

Product 1

HCID 204997883-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-4-(3-phenylpropyl)-4-piperidinol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6.17 g. (10.0 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol, 2.0 g. of 10% palladium-on-carbon and 50 ml. of ethanol is stirred under one atmosphere of hydrogen for 2 hours. The reaction mixture is filtered through diatomaceous earth with ethyl acetate and the filtrate evaporated. The residue is purified via crystallization from ether-pentane to yield the title compound.

Workup

  1. additionA mixture of 6.17 g
  2. filtrationThe reaction mixture is filtered through diatomaceous earth with ethyl acetate
  3. customthe filtrate evaporated
  4. customThe residue is purified via crystallization from ether-pentane

Sources & evidence

ORD record
ord-1ec1e599acb94a80951707d68e29fd1c
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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