Abstract
High field 1H NMR spectra of the commercially-available H1-receptor antagonist 1-methyl-4-diphenylmethox-ypiperidine HCl (1, diphenylpyraline) showed that the protonated base, in aqueous solution, exists as an approximately 1:1 mixture of eq- and ax-4-diphenylmethoxypiperidines (1, 2). In view of the proposed importance of the intramolecular distances between the protonated nitrogen and the centres of gravity of the aromatic substituents with respect to ligand recognition at the H1-receptor the 3-methylpiperidine analogues (4, 6, R = CHPh2) have been chosen to explore this hypothesis and we report the successful syntheses of these two novel conformationally restricted analogues of diphenylpyraline.
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