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

HRID 1276640Notes

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.[OH2:13].OO.N=O>C(O)(C)(C)C>[OH:1][CH:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[N:5]([O:10][CH2:3][C:4]([OH:13])([CH3:12])[CH3:11])[C:4]([CH3:12])([CH3:11])[CH2:3]1

Participants

Conditions

Temperature: 45 °C

Procedure

2,2'-Dipyridyl (0.16 g, 1.0 mmol) and 2.54 g (0.80 mmol) of 5% ferric chloride on silica gel are stirred together in 30 mL of tert-butyl alcohol which is heated to 45° C. To the mixture are added 3.44 g (20.0 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 10 mL of water. A solution of 9.4 g (138 mmol) of 50% aqueous hydrogen peroxide mixed with 20 mL of tert-butyl alcohol is added over four hours at 45-50° C. to the reaction mixture. The temperature is maintained at 45-50° C. for 30 minutes. Analysis by gas chromatography shows that the starting nitroxyl compound is completely reacted to form greater than 90% of the title compound.

Workup

additionis added over four hours at 45-50° C. to the reaction mixture
temperatureThe temperature is maintained at 45-50° C. for 30 minutes
customis completely reacted

Sources & evidence

ORD record: ord-3f567078d3104cfd9d124bcaec371688
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166212

Reaction notes

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