Hydrogen Peroxide → N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

HRID 133631

Reaction equation

HRID 133631 reaction equation
OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13].CS(O)(=O)=O.[CH2:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].CO>[CH:20]1([O:3][N:4]2[C:9]([CH3:10])([CH3:11])[CH2:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:14])[CH3:13])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 6395Methanesulfonic AcidHCID 8078CyclohexaneHCID 986421-Hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine

Product 1

HCID 22019868N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidineYield 35%

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of 20.1 g (0.295 mol) of 50% aqueous hydrogen peroxide is added over 6 hours at 60° C. to a mixture of 8.51 g (50.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperid-4-one, 0.70 g (2.5 mmol) of iron(II) sulfate heptahydrate, 0.3 ml (5 mmol) of methanesulfonic acid, 11 ml of cyclohexane, and 90 ml of methanol. Shortly after the addition is completed, the reaction mixture tests negative for hydrogen peroxide. The reaction mixture is concentrated to afford 4.4 g (35% yield) of the title compound, isolated as a yellow oil. Structure is confirmed by mass spectrometry and NMR analysis.

Workup

  1. additionShortly after the addition
  2. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-a53408cb0ce54faa8f117c9a7ef781f0
Source dataset
uspto-grants-2008_06
Patent number
US07390904B2

Linked notes

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