benzyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → 4-Piperidin-4-ylphenol

HRID 1675102Notes

Reaction equation

HRID 1675102 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11](C(OCC3C=CC=CC=3)=O)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>[Pd].CO>[NH:11]1[CH2:12][CH2:13][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 66788302benzyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 105115114-Piperidin-4-ylphenolYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (37.7 g, 121.86 mmol) and 5% palladium on carbon (7.6 g, 3.57 mmol) in methanol (380 mL) were stirred under an atmosphere of hydrogen at 5 bar and 25° C. for 2 hours. The catalyst was removed by filtration, washed with MeOH and the solvents evaporated. The crude material was triturated with diethyl ether, then the desired product collected by filtration and dried under vacuum to afford 4-(piperidin-4-yl)phenol (20.36 g, 94%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with MeOH
  3. customthe solvents evaporated
  4. customThe crude material was triturated with diethyl ether
  5. filtrationthe desired product collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6c054b9f826644bf82a98a7b90a4a23a
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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