Hydrogen Peroxide → Dibenzylhydroxylamine

HRID 378592Notes

Reaction equation

HRID 378592 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:16]O>C[Re](=O)(=O)=O>[CH2:9]([N:8]([OH:16])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 7656Dibenzylamine

Product 1

HCID 69297DibenzylhydroxylamineYield 50%

Reagents, catalysts & solvents 1

HCID 178477782HCID 178477782, compoundCatalyst

Procedure

U.S. Pat. No. 3,491,151 discloses a method for preparing N,N-dialkylhydroxylamine compounds by allowing hydroxylamines react with alkyl halides, alkyl tosylates or the like. However, this method is also undesirable, because it requires a prolonged reaction time and achieves a yield of no more than about 50%. Tetrahedron Letters, Vol. 37, No. 33 pp. 6025-6028, 1996 discloses a method for synthesizing nitrone compounds by oxidizing dibenzylamine by means of a combination of aqueous hydrogen peroxide and methyltrioxorhenium. According to this synthetic method, an N,N-dibenzylhydroxyl-amine compound is produced in addition to a nitrone compound as a major product. However, its yield is low. Furthermore, the method requires a large amount of methyltrioxorhenium. For these reasons, the method is only disadvantageously applied to practical preparations of N,N-dibenzylhydroxylamine compounds.

Sources & evidence

ORD record
ord-253886566e6e47c68e578d37d49fca69
Source dataset
uspto-grants-2000_02
Patent number
US06031130

Reaction notes

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