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

HRID 980873Notes

Reaction equation

HRID 980873 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-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[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-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

Subsequently, 3.13 g of the 1-benzyl-3-methyl-4-piperidone obtained above was dissolved in 6 ml of ether. The solution was added dropwise to a suspension of 0.44 g of lithium aluminum hydride in 25 ml of ether over 5 minutes while maintaining the temperature at 24°-27° C. Then, the mixture was stirred at 25° C. for 10 minutes, and, 5 ml of water was added thereto under ice-cooling. The mixture was extracted with 30 ml of ether four times. The ether layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain 3.17 g of an oily matter of 1-benzyl-4-hydroxy-3-methylpiperidine.

Workup

  1. temperaturewhile maintaining the temperature at 24°-27° C
  2. temperatureunder ice-cooling
  3. extractionThe mixture was extracted with 30 ml of ether four times
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d580ba0cf2e548029188e50f7859d8d9
Source dataset
uspto-grants-1987_01
Patent number
US04639522

Reaction notes

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