Sodium borohydride → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-ol

HRID 616542Notes

Reaction equation

HRID 616542 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].[BH4-].[Na+]>CO>[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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-one

Product 1

HCID 221822412,6-Diethyl-2,3,6-trimethylpiperidin-4-olYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19.7 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidone were dissolved in 250 ml of methanol, and 3.7 g of sodium borohydride were added thereto in four portions over a period of 1 hour, with stirring. After stirring the mixture for a further 4 hours, it was allowed to stand overnight and was then concentrated by evaporation under reduced pressure; water was added to the concentrated mixture, which was then extracted with benzene. The resulting benzene solution was dried over potassium carbonate and the benzene was distilled off. The residue was distilled under reduced pressure, giving 17.2 g of the title compound as a colourless liquid (bp 125° - 129° C/1.5 mmHg).

Workup

  1. stirringAfter stirring the mixture for a further 4 hours
  2. waitto stand overnight
  3. concentrationwas then concentrated by evaporation under reduced pressure
  4. additionwater was added to the concentrated mixture, which
  5. extractionwas then extracted with benzene
  6. dry with materialThe resulting benzene solution was dried over potassium carbonate
  7. distillationthe benzene was distilled off
  8. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b297029295dc4470aedbb14c248e5d4f
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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