Hydrogen Peroxide → 4-Piperidinol, 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-

HRID 1276650Notes

Reaction equation

HRID 1276650 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([OH:10])[C:4]([CH3:12])([CH3:11])[CH2:3]1.OO.[OH2:15]>C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[OH:1][CH:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[N:5]([O:10][CH2:3][C:4]([OH:15])([CH3:12])[CH3:11])[C:4]([CH3:12])([CH3:11])[CH2:3]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 68508284-Piperidinol, 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-Yield 9%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 6386tert-ButanolSolvent2×

Procedure

A solution of 0.25 g (1.0 mmol) of copper(II) sulfate pentahydrate in 5 mL of water is added to a solution of 0.16 g (1.0 mmol) of 2,2'-dipyridyl in 120 mL of tert-butyl alcohol. To this solution is added 8.6 g (50 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine. A solution of 13.6 g (200 mmol) of 50% aqueous hydrogen peroxide mixed with 13 mL of tert-butyl alcohol is added dropwise to the reaction mixture at 23-40° C. over three hours. The mixture is then stirred at ambient temperature for 72 hours. Gas chromatography shows 9% of the title compound is present in the reaction mixture.

Workup

  1. additionis added dropwise to the reaction mixture at 23-40° C. over three hours

Sources & evidence

ORD record
ord-76ce4f93681c405684026ef646500385
Source dataset
uspto-grants-2000_12
Patent number
US06166212

Reaction notes

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