Hydrochloric Acid → HCID 14078492, compound

Participants

Reaction Steps

O-Benzylhydroxylamine hydrochloride (1a) (13.37 g, 83.74 mmol) was dissolved in 31 mL of methanol and 14 mL of water at 0° C. and the apparent pH adjusted to 4.7 using 6N potassium hydroxide. Heptanal (10.2 mL, 76 mmol) was added, and the pH was maintained at 4.7 while the reaction warmed to room temperature. After the pH change stabilized, the mixture was again cooled to 0° C. and 3.54 g (56.31 mmol) of sodium cyanoborohydride was added. The pH was then lowered to just below 3 and maintained there by the addition of 2N hydrogen chloride in methanol. When the pH change had stabilized, the solution was stirred at pH 3 for 3 h at room temperature. The mixture was then poured into ether (100 mL) and brine (50 mL), and enough 6N potassium hydroxide was added to bring the pH to 9. The aqueous layer was extracted with ether (3×50 mL) and the ether solutions were combined and dried over magnesium sulfate. The solvents were then removed, and the resulting oil distilled at 110°-112° C. (0.1 mm) to give 3.6 g (22%) of (3a): 1H NMR (CDCl3): δ 0.7-1.05 (m, 3H), 1.05-1.73 (m, 10H), 2.92 (t, 2H), 4.7 (s, 2H), 5.3-5.7 (m, 1H), 7.4 (s, 5H): HRMS calcd. for C14H23NO: 221.1778. Found: 221.1721.

Provenance & Evidence