tert-Butyl hydroperoxide → 4-Acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine
Reaction equation
[CH3:1][C:2]([NH:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O])[C:7]([CH3:15])([CH3:14])[CH2:6]1)=[O:3].[C:16]([O:20]O)(C)([CH3:18])[CH3:17].[CH2:22]1[CH2:27]CCC[CH2:23]1>[Mo](=O)(=O)=O>[C:2]([NH:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:20][CH:16]2[CH2:18][CH2:27][CH2:22][CH2:23][CH2:17]2)[C:7]([CH3:15])([CH3:14])[CH2:6]1)(=[O:3])[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A stirred mixture of 10.0 g of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl, 16 ml of 70% aqueous tert-butylhydroperoxide and 0.67 g of molybdenum trioxide in 75 ml of cyclohexane is heated under reflux in a flask fitted with a Dean-Stark apparatus. After 6 ml of water is collected, the reaction mixture is transferred to a Fisher Porter apparatus and heated at 140° C. and 30 psi for 4 hours. The decolorized reaction mixture is filtered and the filtrate is washed with water, aqueous sodium sulfite, brine, dried (MgSO4) and concentrated to give 13.61 g of a white solid. Recrystallization from heptane affords 10.39 g of the title compound as a white crystalline solid, m.p. 140°-44° C.
Workup
- temperatureis heated
- temperatureunder reflux in a flask
- customfitted with a Dean-Stark apparatus
- customAfter 6 ml of water is collected
- customThe decolorized reaction mixture
- filtrationis filtered
- washthe filtrate is washed with water, aqueous sodium sulfite, brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-84b88c07723a4a56b68009f22fc110ed
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05204473
Reaction notes
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