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

HRID 26062Notes

Reaction equation

HRID 26062 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:29])([CH3:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][C:16]=2[O:30]CC2C=CC=CC=2)([OH:14])[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:29][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[C:16]([OH:30])[CH:17]=1)([CH3:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 155715561-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]3-hydroxypiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 155715573-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-3-piperidinolYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8.5 (17.03 mmols) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-hydroxypiperidine, 2.0 g. of 10% palladium-on-carbon and 60 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 evaporated. The residue is recrystallized from ethyl acetate to yield 3.8 g. (70%) of the title compound. A second crop of the title compound 0.396 g. (7%) is obtained from the mother liquor.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth with ethyl acetate
  2. customevaporated
  3. customThe residue is recrystallized from ethyl acetate
  4. customto yield 3.8 g

Sources & evidence

ORD record
ord-527562608acf4740b940b721b5a2be8e
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

Loading…