2190
G. E. MCCASLAND AND DONALD ARTHURSMITH
Vol. 72
Re- a crude hydrochloride, m. p. 163-166', which after t h y e aminocyclohexyl chloride (VIII), m. p. 159-161'. crystallization from benzene gave a colorless product, m. p. recrystallizations from ethanol melted a t 166.5-169 On admixture with pure d,l-trans-2-aminocyclohexanol 163.5-164.5'. Anal. Calcd. for C13HlsONCl: C, 65.68; H, 6.78; hydrochloride (m. p. 175.5-177"), t h e m . p. was 166-172", C1, 14.92. Found: C, 66.03; H , 6.79; C1, 14.78, 14.95. while on admixture with the pure cis-isomer, the m. p. was Hydrolysis of d,Z-trans-2-BenzoylaminocyclohexylChlo- depressed to 142-155 of d,l-trans-2-Benzoylaminocyclohexanol ride (VIII).-A mixture of 0.119 g. of the chloride VIII, to Isomerization the 0-Benzoyl Derivative.-A solution of 0.85 g. of the 10 ml. of ordinary acetic acid (undried), and 0.105 g. of N-benzoyl compound in 80 ml. of dry dioxane was satusilver acetate was heated under reflux with stirring for five with hydrogen chloride and then heated under hours. The silver chloride was removed by filtration, and rated for three hours. Toward the end of the second hour the light red filtrate was made basic with dilute (1: 1) reflux ammonium 'hydroxide solution. The cloudy mixture was crystals began to form. After cooling these amounted t o 0.39 g. (39% yield), m. p. 246-248" (dec.). Sublimathen concentrated a t 20 mm. until crystals began to form, tion t 135-140" (
