Methyl iodide → N-(Benzyloxy)methanamine--hydrogen chloride (1/1)

O-Benzylhydroxylamine hydrochloride (1.59 g, 0.01 mol), di-tert-butyl dicarbonate (2.18 g, 0.01 mol) and N-methyl morpholine (1.1 mL, 0.01 mol) in dichloromethane (40 mL) were stirred at room temperature for 16 hours. The reaction mixture was diluted with ether, washed with 10% NaHSO4, then brine, dried over (Na2SO4), and concentrated. The residue was treated with methyl iodide (1.6 mL, 0.025 mmol) in the presence of NaH (0.4 g, 0.01 mol) in THF at 0° C., then stirred at room temperature for 16 hours. The reaction was quenched with 1N HCl, diluted with ether, washed with brine, dried (Na2SO4), concentrated, purified by silica gel chromatography (20:80/ethyl acetate:hexanes) and treated with 4M HCl in dioxane to give the title compound.

1. washwashed with 10% NaHSO4
2. dry with materialbrine, dried over (Na2SO4)
3. concentrationconcentrated
4. customThe reaction was quenched with 1N HCl
5. additiondiluted with ether
6. washwashed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. custompurified by silica gel chromatography (20:80/ethyl acetate:hexanes)
10. additiontreated with 4M HCl in dioxane

ORD record

ord-42e20d1918c64ee895595fe71d8bfe3a

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887863B2