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

Participants

Reaction Steps

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.

Provenance & Evidence