Hydrogen Peroxide → N-Heptyl-N-methylheptan-1-amine N-oxide

HRID 648177Notes

Reaction equation

HRID 648177 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:17]O>O1CCCC1.[Pt]>[CH2:10]([N+:8]([O-:17])([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH3:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 4413513diheptylmethylamine

Product 1

HCID 53919165N-Heptyl-N-methylheptan-1-amine N-oxide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.6 g of diheptylmethyl amine in 25 ml tetrahydrofuran (THF) was added 12 ml 30% hydrogen peroxide. The reaction mixture was refluxed for 24 hours, cooled to room temperature and then stirred with 0.2 mg platinum black overnight. After filtering the reaction mixture through Hyflo® filter-aid, the THF was removed in vacuo. The aqueous solution was extracted with 100 ml ether. The aqueous portion of the extraction was allowed to stand for several days to allow most of the water to evaporate. The resulting solution was found to be 40% water and 60% diheptylmethyl amine oxide by NMR analysis.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. filtrationAfter filtering the reaction mixture through Hyflo®
  3. filtrationfilter-aid
  4. customthe THF was removed in vacuo
  5. extractionThe aqueous solution was extracted with 100 ml ether
  6. extractionThe aqueous portion of the extraction
  7. waitto stand for several days
  8. customto evaporate

Sources & evidence

ORD record
ord-a522f29fdd9d487fa21d8c579e23e8b2
Source dataset
uspto-grants-1983_10
Patent number
US04411893

Reaction notes

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