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

HRID 1395210Notes

Reaction equation

HRID 1395210 reaction equation
[OH:1]O.[C:3]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:23])[CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1)([CH2:6][CH3:7])([CH3:5])[CH3:4]>C(O)(C)C.[Pt]>[C:3]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH:15]([CH3:23])[CH2:16][N+:17]2([O-:1])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[CH:12][CH:13]=1)([CH2:6][CH3:7])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 190989441-[3-(p-Tert.amyl-phenyl)-2-methyl-propyl]-piperidine

Product 1

HCID 203405661-[3-(p-Tert.amyl-phenyl)-2-methyl-propyl]-piperidine-1-oxide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

7.2 g of 30% hydrogen peroxide are added dropwise at 40° C. to a solution of 5.8 g of 1-[3-(p-tert.amyl-phenyl)-2-methyl-propyl]-piperidine in 20 ml of isopropanol and this addition is repeated after 24 hours. After stirring at 40° C. for 60 hours, the mixture is cooled and the excess hydrogen peroxide is decomposed by 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 dried in a high vacuum. There is obtained pure 1-[3-(p-tert.amyl-phenyl)-2-methyl-propyl]-piperidine-1-oxide; nD20 =1.5180.

Workup

  1. additionthis addition
  2. temperaturethe mixture is cooled
  3. filtrationThe solution is filtered
  4. customthe filtrate is evaporated
  5. extractionextracted with hexane
  6. customThe aqueous solution is subsequently evaporated
  7. customthe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-5ff15de35f5145cc8cea553fe2009f56
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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