Benzyl Bromide → N,O-Dibenzylhydroxylamine

HRID 414493Notes

Reaction equation

HRID 414493 reaction equation
[CH2:1]([O:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[CH2:10]([NH:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 102313O-Benzylhydroxylamine

Product 1

HCID 11063773N,O-DibenzylhydroxylamineYield 33.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4 g of O-benzylhydroxylamine, 4.28 g of benzyl bromide, and 12 g of K2CO3 in 50 ml of ethanol was stirred at 50° C. overnight. After removal of organic solvent, water was added to the residue and the mixture was then extracted with ethyl acetate. The combined extracts were dried and evaporated to give 4 g of crude product. Purification by dry column chromatography gave 1.8 g of oily product.

Workup

  1. customAfter removal of organic solvent, water
  2. additionwas added to the residue
  3. extractionthe mixture was then extracted with ethyl acetate
  4. customThe combined extracts were dried
  5. customevaporated
  6. customto give 4 g of crude product
  7. customPurification
  8. customby dry column chromatography

Sources & evidence

ORD record
ord-addcd505782e4867bc2047d110324372
Source dataset
uspto-grants-1988_12
Patent number
US04792560

Reaction notes

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