Stability of oxetacain and the structure of its degradation products
Refluxed acid aqueous solutions of oxetacain (1) show 3 degradation products. 1 is decomposed at room temperature (20 °C, 480 d) 10%. 7 degradation products of crystalline 1 are detectable in the temperature-moisture test. At room temperature no other product than 1 appears. Under normal storage conditions a 5-year stability for acid aqueous solutions and a more than 10-year stability for crystalline 1 are estimated. Small amounts of the degradation products were isolated by TLC and HPLC. According to MS, UV and IR analysis their structures are mephentermin (2), a morpholinone derivative (3), a carboxylic acid derivative of 1 (4), a mono-C-demethyl-1 (5) and a mono-N-de(1-phenyl-2-methyl-propyl)-1 (6). The structures of 2 other degradation products are unknown. MS fragmentation mechanisms are discussed.
Gober,Franke,Lisowski
p. 584 - 587
(2007/10/02)
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