Methyl iodide → (Benzyloxy)(methyl)amine

HRID 1165060Notes

Reaction equation

HRID 1165060 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:11]N(P(N(C)C)(N(C)C)=O)C.CI>O.[Cl-].[Na+].O>[CH2:2]([O:9][NH:10][CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 13417387(Benzyloxy)(methyl)amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of O-benzylhydroxyl amine hydrochloride (1.59 g, 10 mmole) in 15 ml of dry HMPA containing dry sodium bicarbonate (3.36 g, 40 mmole) was added methyl iodide (1.5 g, 11 mmole). After 5 hours the resulting mixture was diluted with 30 ml of water and 20 ml of brine and extracted three times with ethyl ether. The extracts were combined, washed, dried and evaporated to produce the crude product as an oil. The oil was chromatographed to afford 800 mg of title C compound, with consistent spectral data.

Workup

  1. extractionextracted three times with ethyl ether
  2. washwashed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-da44ad78e45f4f74b36a36ecf0e8b953
Source dataset
uspto-grants-1990_03
Patent number
US04906667

Reaction notes

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