Dibenzylamine → Dibenzylhydroxylamine

HRID 359579

Reaction equation

HRID 359579 reaction equation
CC1(C)O[O:3]1.[CH2:6]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CC(C)=O>[CH2:14]([N:13]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 115197Dimethyldioxirane

Product 1

HCID 69297DibenzylhydroxylamineYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A solution of 0.051 M dimethyldioxirane in acetone (32.9 ml, 1.67 mmol) was added to a cold stirred solution of N,N-dibenzylamine (Aldrich; 0.331 g, 1.67 mmol) in acetone (5 ml). The mixture was stirred for fifteen minutes in an ice bath. Evaporation of the solvent on the rotary evaporator gave a white crystalline solid. The solid was dissolved in acetone and the solution dried with anhydrous Na2SO4. The solvent was removed to give a chromatographically homogeneous white solid (0.352 g, 98% yield). Measured mp was 121-122; reported mp is 122-123 (DeLaMare et al 1963).

Workup

  1. customEvaporation of the solvent
  2. customon the rotary evaporator
  3. customgave a white crystalline solid
  4. dry with materialthe solution dried with anhydrous Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-de813412e5ae4b6b82cee1cde65dbf21
Source dataset
uspto-grants-1991_03
Patent number
US05001233

Linked notes

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