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

HRID 1155831Notes

Reaction equation

HRID 1155831 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 g. (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. additionA mixture of 8.5 g
  2. filtrationThe reaction mixture is filtered through diatomaceous earth with ethyl acetate
  3. customevaporated
  4. customThe residue is recrystallized from ethyl acetate
  5. customto yield 3.8 g

Sources & evidence

ORD record
ord-7326d2ddbd7d4b918039b008c0a441e3
Source dataset
uspto-grants-1982_06
Patent number
US04332942

Reaction notes

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