Piperidine → 4-(Piperidin-1-yl)phenol

HRID 2354033Notes

Reaction equation

HRID 2354033 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1(=O)[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1>C(O)C.[C].[Pd]>[OH:13][C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 125111,4-Cyclohexanedione

Product 1

HCID 904524-(Piperidin-1-yl)phenolYield 43.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.85 g of piperidine, 1.68 g of 1,4-cyclohexanedione and 40 mg of 10% palladium-carbon were heated with stirring in 40 ml of ethanol at 50° C. to 60° C. and reacted for 8 hours under air bubbling. During the reaction, ethanol was added as needed. After the completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resultant was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) and purified by silica gel column chromatography again, and 0.668 g of 1-(4-hydroxyphenyl)piperidine was obtained (yield 43.4%).

Workup

  1. customreacted for 8 hours under air
  2. custombubbling
  3. customDuring the reaction, ethanol
  4. additionwas added
  5. customAfter the completion of the reaction
  6. customthe catalyst was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resultant was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
  9. custompurified by silica gel column chromatography again

Sources & evidence

ORD record
ord-4d0f3a4a48f44ec1ad5e42423237ca77
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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