Sodium Hydroxide → 1,2,2,6,6-Pentamethyl-4-piperidone oxide

HRID 377367

Reaction equation

HRID 377367 reaction equation
I.[CH3:2][N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6](=[O:11])[CH2:5][C:4]1([CH3:13])[CH3:12].Cl.N[OH:16].[OH-].[Na+]>O>[CH3:2][N+:3]1([O-:16])[C:8]([CH3:9])([CH3:10])[CH2:7][C:6](=[O:11])[CH2:5][C:4]1([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 223975731,2,2,6,6-Pentamethyl-4-piperidone hydroiodide

Product 1

HCID 193586881,2,2,6,6-Pentamethyl-4-piperidone oxideYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 1,2,2,6,6-pentamethyl-4-piperidone hydroiodide (3 g, 10.0 mmol) and hydroxylamine hydrochloride (980 mg, 14 mmol) in water (6 ml) was stirred at RT for 15 min. Solid NaOH was added until basic pH and thickening of the suspension. Water (3 ml) was added and stirring at RT was continued overnight. The suspension was filtered and the solid washed with water (few ml) and dried. The solid was then dissolved in Et2O, the solution was dried (MgSO4) and concentrated to give after drying pure title compound (1.55 g, 8.41 mmol, yield 83.3%) as white crystals.

Workup

  1. stirringstirring at RT
  2. waitwas continued overnight
  3. filtrationThe suspension was filtered
  4. washthe solid washed with water (few ml)
  5. customdried
  6. dissolutionThe solid was then dissolved in Et2O
  7. dry with materialthe solution was dried (MgSO4)
  8. concentrationconcentrated
  9. customto give

Sources & evidence

ORD record
ord-4092f7a061de4dd6b27612bb696f51e2
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Linked notes

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