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

HRID 1395353Notes

Reaction equation

HRID 1395353 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].[OH-].[Na+].[BH4-].[Na+]>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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 221822132,6-Diethyl-2,3,6-trimethylpiperidin-4-one

Product 1

HCID 221822412,6-Diethyl-2,3,6-trimethylpiperidin-4-olYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 2-liter, 3-necked flask equipped with a stirrer, condenser, thermometer and nitrogen inlet were placed 197.3 g (1.0 moles) of 2,6-diethyl-2,3,6-trimethyl piperidin-4-one, 500 ml of 2 N sodium hydroxide and 500 ml of absolute ethanol. To the stirred reaction mixture, maintained under nitrogen, was added portionwise 18.92 m (0.5 moles) of sodium borohydride over a 11/2 hour period. The reaction mixture was then stirred overnight at room temperature. The reaction mixture was decanted into a 4-liter separatory funnel and 2 liters of water were added. The aqueous layer was separated and the organic layer diluted with 500 ml of ether. The ether solution was washed with 2×1 l water. The first aqueous layer was extracted with 2×50 ml of ether, then the combined ether extracts were washed with 500 ml of water. The ether layers were combined, dried over 4A molecular sieves and evaporated under reduced pressure, giving 187.4 g of the desired 2,6-diethyl-2,3,6-trimethyl piperidin-4-ol which was purified further by vacuum distillation, b.p. 111°-115°/6 mm.

Workup

  1. customIn a 2-liter, 3-necked flask equipped with a stirrer, condenser
  2. customTo the stirred reaction mixture
  3. temperaturemaintained under nitrogen
  4. customThe reaction mixture was decanted into a 4-liter separatory funnel
  5. addition2 liters of water were added
  6. customThe aqueous layer was separated
  7. additionthe organic layer diluted with 500 ml of ether
  8. washThe ether solution was washed with 2×1 l water
  9. extractionThe first aqueous layer was extracted with 2×50 ml of ether
  10. washthe combined ether extracts were washed with 500 ml of water
  11. dry with materialdried over 4A molecular sieves
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d55f2938fd684c408a714914ea9cd1ec
Source dataset
uspto-grants-1980_05
Patent number
US04203890

Reaction notes

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