Hydrochloric Acid → O-Benzyl-N-(4-cyanobutyl)hydroxylamine

Beteiligte Stoffe

Reaktionsschritte

O-Benzylhydroxylamine hydrochloride (4.7 g, 29.7 mmol) was mixed with 5 mL of water and 11 mL of methanol at 0° C. and the apparent pH adjusted to 4.7 using 6N potassium hydroxide. The aldehyde, 4-cyanobutanal (1), [Izawa, supra] (2.6 mL, 27 mmol) was added to the hydroxylamine and the mixture allowed to warm to room temperature. The pH was maintained by the addition of further 6N potassium hydroxide. After 1 h, the reaction was cooled to 0° C., and sodium cyanoborohydride (1.26 g, 20 mmol) was added. The pH was adjusted to 3 and maintained by addition of saturated hydrogen chloride in methanol. When the pH stabilized, the reaction was warmed to room temperature and stirred for 3 h at a pH of 3. The reaction mixture was then poured into ether and made basic with 6N potassium hydroxide. The aqueous layer was extracted with ether (3× 50 mL). The extracts were combined, washed with brine, and dried over magnesium sulfate. The solvents were removed and the resulting liquid distilled at 150°-151° C. (0.6 mm) to give 4.65 g (84%) of (3): 1H NMR (CDCl3): δ 1.56-1.85 (m, 4H), 2.20-2.45 (m, 2H), 2.85-3.10 (m, 2H), 4.7 (s, 2H), 5.53 (t, 1H), 7.4 (s, 5H); IR (CHCl3): 3040, 2930, 2860, 2240, 1500, 1450, 1430, 1360, 1210; Anal. Calcd. for C12H16N2O: C, 70.54; H, 7.91. Found: C, 70.51; H, 7.91.

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