Kinetics of 5-(1-Phenyl-4-piperazinyl)methyl-2-amino-2-oxazoline Hydrolysis by High Performance Liquid Chromatography

Abstract

The effect of pH on the stability of 5-(1-phenyl-4-piperazinyl)methyl-2-amino-2-oxazoline (COR 3224), a novel antidepressant, was determined by HPLC at different pH (1, 3, 6, 7.4) at 100°C. One degradation product was isolated at pH 1 and identified as the 5-(1-phenyl-4-piperazinyl)methyl-2-oxazol-idinone. A hydrolysis kinetic study was carried out over a range of pH (1-7.4). The degradation followed a pseudo-first-order kinetics with respect to COR 3224 and was accelerated by an increase in pH.

Notes

Physical and spectral data for compound II: F(°C) 153 (Ethanol); Formula: C₁₄H₁₉N₃O₂; IR (KBr) v cm⁻¹: 1730 (C=O), 3200 (NH); NMR ¹H (CDCl₃) δ ppm: 7.05 (m, 5H, Har), 5.10 (s, 1H, NH), 4.82 (m, 1H, 5-H), 3.63 (m, 2H, 4-H), 3.2 (m, 4H, CH_2piperazine), 2.72 (m, 6H, CH_2piperazine and NCH₂); NMR ¹³C (CDCl₃) δ ppm: 157.7 (C=O), 148.8, 129.1, 120.6, 116.2 (C_phenyl), 70.3 (C-5), 58.1 (CH₂), 51.1 and 45.4 (C_piperazine), 43.2 (C-4).