Ethanol → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidine

HRID 1155833Notes

Reaction equation

HRID 1155833 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][NH:18][CH2:19][CH2:20][CH:21]=2)=[C:12]([OH:22])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)C.[H][H]>[Pd].C(OCC)(=O)C>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12]([OH:22])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 155715613-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 155715583-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidineYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7.4 g. (24.5 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine and 2.0 g. of 10% palladium-on-carbon in 150 ml. of ethanol and 75 ml. of ethyl acetate is stirred under one atmosphere of hydrogen for 2.5 hours. The reaction is filtered through diatomaceous earth and evaporated. Crystallization of the residue from ether-pentane gave 4.6 g. (62%) of the title compound.

Workup

  1. additionA mixture of 7.4 g
  2. filtrationThe reaction is filtered through diatomaceous earth
  3. customevaporated
  4. customCrystallization of the residue from ether-pentane
  5. customgave 4.6 g

Sources & evidence

ORD record
ord-4aea9a63763e459ea2ac3187addec0e0
Source dataset
uspto-grants-1982_06
Patent number
US04332942

Reaction notes

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