1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1,2,5,6-tetrahydropyridine → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidine

HRID 26065Notes

Reaction equation

HRID 26065 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:28])([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][C:15]=2[O:29]CC2C=CC=CC=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:28][C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[C:15]([OH:29])[CH:16]=1)([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 204997811-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1,2,5,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 155715583-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidineYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.2 g. (8.73 mmols) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1,2,5,6-tetrahydropyridine, 4.0 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, evaporated and the residue again dissolved in ethyl acetate and filtered. The filtrate is evaporated and the residue crystallized in ether to yield 1.1 g. (42%) of the title compound.

Workup

  1. additionA mixture of 4.2 g
  2. filtrationThe reaction mixture is filtered through diatomaceous earth with ethyl acetate
  3. customevaporated
  4. dissolutionthe residue again dissolved in ethyl acetate
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. customthe residue crystallized in ether
  8. customto yield 1.1 g

Sources & evidence

ORD record
ord-79aafa1cc7214830822e6fe078a7bad2
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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