ChemInform Abstract: SYNTHESIS, PHYSICO‐CHEMICAL PROPERTIES AND PHARMACOLOGICAL STUDIES OF BUDIPINE AND RELATED 4,4‐DIPHENYLPIPERIDINES

Abstract

Nach verschiedenen Verfahren, z.B. aus dem Piperidon (IV), aus den Benzoylpiperidinen (VI) oder durch Alkylierung von (Ia), werden die N‐Alkyl‐diphenylpiperidine (Ib) bis (Id) hergestellt.

Synthesis of Aryl-Substituted Piperidines by Superacid Activation of Piperidones

“…The aryl-substituted piperidines have been of particular interest because of their strong interaction with monoamine receptors associated with the central nervous system . There have been some reports of the preparation of aryl-substituted piperidines from piperidones in AlCl 3 −benzene solution, and several reports have appeared in which intramolecular electrophilic aromatic substitution involving piperidones was accomplished with strong Bronsted acids . In this paper, we describe the trifluoromethanesulfonic acid-catalyzed condensations of piperidones and related systems with aromatic compounds to give diarylpiperidines.…”

Use of 4-piperidones in one-pot syntheses of novel, high-molecular-weight linear and virtually 100%-hyperbranched polymers

“…However, there are surprisingly few reports concerning the preparation of aryl-substituted piperidines by acid-catalyzed reactions of piperidones with aromatic compounds. 3 Recently, it was shown that diaryl piperidines may be prepared in good to excellent yields by the reaction of piperidones with benzene in the presence of trifluoromethanesulfonic acid. 4,5 We have performed calculations of the TFSA-catalyzed reaction of piperidone with biphenyl and found that the high reactivity of the carbonyl group is due to the inductive effect of a protonated heteroatom rather than through-space electrostatic effects.…”