A novel synthesis of 2-aryl-4-piperidones by mannich cyclization of iminoketals

2-Aryl-4-piperidones have been synthesized by condensation between an aromatic aldehyde and a β-aminoketone ethylene ketal, and further cyclization of the resulting iminoketal with dry hydrogen chloride or anhydrous p-toluensulfonic acid. Alternatively, reaction of the above iminoketals with methyl fluorosulfonate followed by dry hydrogen chloride treatment and acid hydrolysis gives directly N-methyl-4-piperidones. The application of these reactions to the synthesis of some 2-aryl-3-acetylpyrrolidine systems is also described.