Water → 1-Benzyl-3-methylpiperidin-4-ol

HRID 481775Notes

Reaction equation

HRID 481775 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O>C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 136114921-Benzyl-3-methylpiperidin-4-olYield 68.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution (15 ml) of 3.98 g of 1-benzyl-3-methyl-4-piperidone in diethyl ether was added to a suspension (10 ml) of 0.78 g of aluminum lithium hydride in diethyl ether in an ice bath, and the solution was heated under ref lux for 3 hours. Water was added to the solution, and the solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous solution of hydrogen chloride. The solution was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography, and from the fractions eluted with chloroform-methanol (19:1 v/v) was obtained 2.76 g of 1-benzyl-4-hydroxy-3-methylpiperidine, which was an oily product (yield: 69%).

Workup

  1. temperaturethe solution was heated under ref lux for 3 hours
  2. extractionthe solution was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous solution of hydrogen chloride
  4. dry with materialThe solution was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography
  7. washfrom the fractions eluted with chloroform-methanol (19:1 v/v)

Sources & evidence

ORD record
ord-e41368919029450cbe0becd9c01a4a92
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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