H. V. Maulding, D. Brusco, J. Polesuk
Aug 1, 1972
Citations
0
Influential Citations
6
Citations
Journal
Journal of pharmaceutical sciences
Abstract
Factors involved in the relative reaction rates of hydrolysis of certain 5-aminodibenzo[a, b]cycloheptanes were investigated. Several compounds were prepared for examination of their breakdown in acidic media at various temperatures. Synthesis was carried out through condensation of 5-chlorodibenzo[a, b]cycloheptane with the appropriate amine in benzene. Kinetics were followed by the acid-dye method employing methyl orange as the anionic species of the ion-pair. Generally, the colored complexes were readily extractable into chloroform at pH 3.44. Considerable variation in the hydrolytic velocities of the several amines was noted, and the results are given along with Arrhenius parameters and other pertinent data for selected compounds. The degradation is characterized by cleavage of a carbon—nitrogen (amino) bond at the 5-position of the fused ring system leading to the secondary amine and 5-hydroxydibenzo[a, b]cycloheptane as well as other nonnitrogenous products. The transformation exemplifies breakage of a carbon—nitrogen linkage in dilute acidic solution under rather mild conditions dependent upon substituents on the amino group. The process possibly proceeds via a carbonium-ion intermediate or its equivalent.