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

HRID 444341Notes

Reaction equation

HRID 444341 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-f641f607ebff42e186857a6c4ef15dd0
Source dataset
uspto-grants-1981_04
Patent number
US04263438

Reaction notes

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