Ethanol → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-ol

HRID 276119Notes

Reaction equation

HRID 276119 reaction equation
[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[C:7](=[O:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].C(O)C>>[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([OH:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-one

Product 1

HCID 221822412,6-Diethyl-2,3,6-trimethylpiperidin-4-ol

Conditions

Temperature
50 °C

Procedure

To a solution of 118.2 g (0.6 mol) 2,6-diethyl-2,3,6-trimethyl-4-oxopiperidine in 1000 ml ethanol 18.2 g (0.4 mol) sodium borohydride are added in portions and the temperature is kept below 30° C. Subsequently the solution is stirred for 2 hours at 50° C. Ethanol is distilled off, 500 ml water are added to the residue which is subsequently extracted several times with CH2Cl2. The extract is dried over Na2SO4 and the solution is filtered. After removing the solvent 116 g (97%) 2,6-diethyl-2,3,6-trimethyl-4-hydroxypiperidin are obtained as yellowish liquid.

Workup

  1. customis kept below 30° C
  2. distillationEthanol is distilled off
  3. addition500 ml water are added to the residue which
  4. dry with materialThe extract is dried over Na2SO4
  5. filtrationthe solution is filtered
  6. customAfter removing the solvent 116 g (97%) 2,6-diethyl-2,3,6-trimethyl-4-hydroxypiperidin
  7. customare obtained as yellowish liquid

Sources & evidence

ORD record
ord-e714e0ad50fd4fad8d09b69743d6bc90
Source dataset
uspto-grants-2002_03
Patent number
US06353107B1

Reaction notes

Loading…