Sodium cyanoborohydride → n-[3-(3,4-Dichlorophenyl)-propyl]-o-methyl-hydroxylamine

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Reaction Steps

Reduction of 3-(3,4-dichlorophenyl)-propionaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil after chromatography on silica gel and distillation in vacuo (48% yield): bp 75-80° C./0.3 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CHCl3) δ (ppm): 1.81 (2H, m, CH2), 2.63 (2H, t, J=7.8 Hz, CH2), 2.90 (2H, t, J=7.1 Hz, CH2), 3.52 (3H, s, OCH3), 5.55 (broad, NH), 7.01 (1H, dd, J=2.0 Hz and J=8.1 Hz, aromatic), 7.27 (1H, broad d, aromatic), 7.32 (1H, d, J=8.1 Hz, aromatic). The hydrochloride salt was obtained as a white solid: mp 81-83° C. Anal. calcd for C10H13Cl2NO—HCl: C, 44.39; H, 5.22; N, 5.18. Found: C, 44.57; H, 5.05; N, 5.18.

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