Hydrogen Peroxide → Dibenzylhydroxylamine

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Reaction Steps

Dibenzylamine (3.0 g, 0.0152 mole) was added with ethyl acetate (15 ml) and anhydrous magnesium sulfate (3 g), and the mixture was stirred under ice cooling. A solution of methyltrioxorhenium (0.0114 g, 0.0457 mmole) dissolved in 35% aqueous hydrogen peroxide (1.8 g, 0.018 mole) was added dropwise to the mixture over 1 hour so as to keep internal temperature at 5° C. to 10° C. After the reaction mixture was stirred at the same temperature for 1 hour, the magnesium sulfate was removed by filtration, and the filtrate was added with a solution of oxalic acid (1.23 g, 0.0137 mole) dissolved in acetone (7 ml). The mixture was stirred for 30 minutes under ice cooling, and the precipitated crystals were collected by filtration to obtain oxalic acid salt of N,N-dibenzylhydroxylamine (3.0 g, yield: 65.2%) having melting point of 152-153° C. Chemical structure of the product was analyzed by 1H-NMR, mass spectrometry and elemental analysis. 1H-NMR (DMSO-D6) σ (ppm) (multiplicity, integrated value): 7.45-7.12 (m, 11H), 3.85 (s, 4H). Elemental analysis, calculated for C16H17N1O5 : C, 63.36; H, 5.65; N, 4.62, found: C, 63.30; H, 5.65; N, 4.62.

Provenance & Evidence