Hydrogen Peroxide → N-Butyl-N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)acetamide

HRID 582945Notes

Reaction equation

HRID 582945 reaction equation
[CH2:1]([N:5]([CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]1)[C:6](=[O:8])[CH3:7])[CH2:2][CH2:3][CH3:4].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=[O:24].OO>CO>[CH2:1]([N:5]([CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([OH:24])[C:11]([CH3:17])([CH3:18])[CH2:10]1)[C:6](=[O:8])[CH3:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6049Ethylenediaminetetraacetic AcidHCID 212252644-(N-butylacetamido)-2,2,6,6-tetramethylpiperidine

Product 1

HCID 66649397N-Butyl-N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred 50° C. solution of 13.3 g of N-butyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide, 0.075 g of sodium tungstate-dihydrate and 0.075 g of ethylenediamine-tetraacetic acid in 25 mL of methanol is added 35 mL of 30% aqueous hydrogen peroxide over a three hour period. After the addition is complete, the reaction mixture is stirred another two hours. The reaction mixture is then partitioned between diethyl ether and water. The organic phase is washed with water, 1% aqueous hydrogen chloride and then water. After drying over anhydrous magnesium sulfate and concentrating, the title compound is obtained as a red solid. After crystallization from hexane, the compound melts at 84-85° C.

Workup

  1. additionAfter the addition
  2. customThe reaction mixture is then partitioned between diethyl ether and water
  3. washThe organic phase is washed with water, 1% aqueous hydrogen chloride
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-8f4eb768dc1540d89c81feade6e99f3a
Source dataset
uspto-grants-1999_07
Patent number
US05928558

Reaction notes

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