N-phenylmethoxymethanimine → (Benzyloxy)(methyl)amine

HRID 530055Notes

Reaction equation

HRID 530055 reaction equation
Cl.CCO.[CH2:5]([O:12][N:13]=[CH2:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCO>[CH2:5]([O:12][NH:13][CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 561610N-phenylmethoxymethanimineHCID 21887872Ethanol hydrochloride

Product 1

HCID 13417387(Benzyloxy)(methyl)amineYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1M HCl/EtOH solution (50 mL) was added dropwise to the solution of formaldehyde O-benzyl-oxime (3.85 g, 28.48 mmol) in EtOH at 0° C. The mixture was stirred at room temperature for 1 hour, volatiles were removed in vacuo. The residue was dissolved in dichloromethane (100 mL), washed with saturated NaHCO3 solution (75 mL), water (75 mL), and dried over Na2SO4. The product was purified by flash column chromatography using gradient elution from petroleum ether/EtOAc (9:1) to petroleum ether/EtOAc (7:1) to yield O-benzyl-N-methyl-hydroxylamine (1.72 g, 44%). 200 MHz 1H NMR (CDCl3, ppm) 7.40-7.27 (5H, m), 5.53 (1H, br s), 4.71 (2H, s), 2.73 (3H, s).

Workup

  1. customvolatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. washwashed with saturated NaHCO3 solution (75 mL), water (75 mL)
  4. dry with materialdried over Na2SO4
  5. customThe product was purified by flash column chromatography
  6. washelution from petroleum ether/EtOAc (9:1) to petroleum ether/EtOAc (7:1)

Sources & evidence

ORD record
ord-13703631ca374d23a643d89ca94c1f12
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

Loading…