In the gas phase, the chair-chair conformation predominates[1] A convenient route to synthesize the bispidine molecule involves a pent-1-en-3-one and a prop-2-en-1-amine leading to a bis(carbethoxyethyl)allylamine which converts in 1-allylpiperidin-4-one by acid hydrolysis and decarboxylation.
[3] The bispidine unit can be chemically functionalized in several positions of its rigid bicyclic scaffold leading to a large number of bispidine-type ligands.
The first step includes a reaction between a compound containing acidic C-H hydrogens, an aldehyde and a primary amine, using a predefined molar ratio of 1:2:1, respectively, leading to a piperidone.
Many computational studies and others based on nuclear magnetic resonance (1H and 13C NMR), X-ray crystallography and Raman spectroscopy have been done to investigate the different conformational entities of bispidine derivatives.
[17] It has been also found out that they exhibit high affinity and selectivity to ĸ-opioid receptors and many studies concerning the influence of structural variation towards their biological activity were also reported.
Bispidine derivatives have been used as ligands to build novel one-dimensional coordination polymers, showing an interesting influence on the dynamic behaviour of these hybrid systems.