Ethanol → HCID 86074476, compound

HRID 2354035Notes

Reaction equation

HRID 2354035 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(=O)[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.[CH2:16](O)C>[C].[Pd]>[OH:14][C:11]1[CH:12]=[CH:13][C:1]([N:2]2[CH2:7][CH2:6][CH:5]([CH3:16])[CH2:4][CH2:3]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 12291N-MethylpiperidineHCID 125111,4-Cyclohexanedione

Product 1

HCID 86074476HCID 86074476, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

1.00 g of 1-methylpiperadine, 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 (ethyl acetate:methanol=3:1) and 1.26 g of 1-(4-hydroxyphenyl)-4-methylpiperadine was obtained (yield 65.5%).

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 (ethyl acetate:methanol=3:1)

Sources & evidence

ORD record
ord-4c00e2d3b4c34fafa61e4a9a98a0a713
Source dataset
uspto-grants-2010_07
Patent number
US07750156B2

Reaction notes

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