A new piperazine: Spectroscopic and theoretical conformational studies

Abstract

The reaction of benzylamine with the N-tosylaziridine prepared from (S)-serine and bearing an amide group at C2 afforded a single open chain compound, in contrast to the lack of regioselectivity for the ring opening of the analogous 2-carbalkoxy derivative. The (S)-amide substituted piperazine was prepared by N,N′-bisalkylation of the corresponding open chain compound. Theoretical calculations for the piperazine and NMR experiments indicated that for all three most stable conformations the amide group is axially positioned.