Aqueous degradation of N-(hydroxymethyl)phthalimide in the presence of specific and general bases. Kinetic assessment of N-hydroxymethyl derivatives of nitrogen heterocycles as possible prodrugs.

The conversion of N-(hydroxymethyl)phthalimide (NHPH) to phthalimide could not be detected within 300 s at pH 9.0, whereas in 0.18 M NaOH complete conversion of NHPH to phthalimide was observed within 50 s. In the presence of 0.2-0.4 M 1,4-diazabicyclo[2.2.2]octane buffer solutions (pH 9.30-9.54), 40-60% conversion of NHPH to phthalimide occurred within 90-120 s. The initial concentration of NHPH affected the extent of conversion of NHPH to phthalimide.