4-(1,2,2,6,6-Pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol → 4-(1,2,2,6,6-Pentamethyl-piperidin-4-yl)-phenol

HRID 237746Notes

Reaction equation

HRID 237746 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:4][C:3]1([CH3:18])[CH3:17]>[Pd].CO>[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[CH2:4][C:3]1([CH3:18])[CH3:17]

Participants

4

Reactant 1

HCID 685241834-(1,2,2,6,6-Pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol

Product 1

HCID 196012004-(1,2,2,6,6-Pentamethyl-piperidin-4-yl)-phenolYield 60.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.33 g of palladium on activated carbon (10%) was added a solution of 4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol (3.27 g, 13.3 mmol) in methanol (100 mL). This mixture was stirred at room temperature under H2 (1 atm) for 2 hours. The catalyst was filtered and the filtrate concentrated. The residue was purified by chromatography on silica gel (eluting with 7N NH3 in methanol/dichloromethane) to give 4-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-phenol (2 g 60%) as a white foam.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by chromatography on silica gel (eluting with 7N NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-f9b9188a8ab0406a900b746cca382543
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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