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

HRID 584855Notes

Reaction equation

HRID 584855 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-hydroxypiperidine 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-hydroxypiperidine
  7. customare obtained as yellowish liquid

Sources & evidence

ORD record
ord-98da277e7ab64eb3afa0280e291d8941
Source dataset
uspto-grants-2005_08
Patent number
US06927295B2

Reaction notes

Loading…