Journal of Pharmaceutical Sciences p. 1028 - 1031 (1992)
Update date:2022-07-30
Topics:
Lambert
Timmer
Walters
Hsu
The kinetics and mechanisms of the racemization and cyclization reactions of ibutilide are described. The cyclization reaction yields a bell-shaped rate-pH curve consistent with a change in rate-determining step. It is hypothesized that the hydroxyl group leaves to form a carbocation intermediate; this is followed by nucleophilic attack by the amine. This mechanism is supported by kinetic analysis, aniline trapping of carbocation intermediate, and observation of all four stereo-isomers of the resulting quaternary ammonium compound. Whereas racemization can also progress through the carbocation intermediate, a direct S(N)2 mechanism appears to be the major route for the racemization reaction.
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