Hydrogen Peroxide → 1-[3-(p-Tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine-1-oxide

HRID 1733270Notes

Reaction equation

[OH:1]O.[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]([CH3:22])[CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>C(O)(C)C.[Pt]>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]([CH3:22])[CH2:15][N+:16]2([O-:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 40 °C

Procedure

5.4 g of 30% hydrogen peroxide are added dropwise at 40° C. to a solution of 5.4 g of 1-[3-(p-tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine in 40 ml of isopropanol, this addition being repeated after 24 hours. After stirring at 40° C. for 60 hours, the mixture is cooled and the excess hydrogen peroxide is decomposed by the addition of platinum sponge. The solution is filtered, the filtrate is evaporated, the residue is taken up in 50 ml of water and extracted with hexane. The aqueous solution is subsequently evaporated and the residue is crystallised from pentane. There is obtained pure 1-[3-(p-tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine-1-oxide of melting point 82°-88° C. (hydrate).

Workup

additionthis addition
temperaturethe mixture is cooled
filtrationThe solution is filtered
customthe filtrate is evaporated
extractionextracted with hexane
customThe aqueous solution is subsequently evaporated
customthe residue is crystallised from pentane

Sources & evidence

ORD record: ord-af34c518c0ed4e74b4032974e12c38e3
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04241058

Reaction notes

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