Abstract
An x-ray diffraction structural analysis was carried out using λCu radiation with 2975 reflections, θ≤64° to R=0.073 for the bisulfate of the major component of the narcotic analgesic, phenaridine (1-(2-phenethyl)2,5-dimethyl-4-(N-propionylanilino)-piperidine citrate). The crystals studied obtained from cyclohexanone are a double solvate containing 1/2 randomly disordered cyclohexanone molecule and one water molecule per formal salt unit. The unit cell parameters for the monoclinic crystals are as follows: a=15.231(2), b=14.946(2), c=13.070(2) Å, β-104.23(1)°, space group P21/c, Z=4. The methyl groups in the compound studied occupy the 2-equatorial and 5-axial positions relative to the piperidine ring. Taking account of the equatorial positions of the substitutents at the 1- and 4-positions of the piperidine ring, the compound designated should be designated the rel-(1R,2R,4S,5R) isomer. The cation has an extended conformation with ordinary geometric parameters. The relative arrangement of the pharmacophoric groups in the cation (benzene rings A and F, piperidine ring D, and the amide fragment) is similar to that for the groups in “T-shaped” morphine-like molecules.
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Institute of Fine Organic Chemistry, Academy of Sciences of the Armenian SSR. Translated from Zhurnal Strukturnoi Khimii, Vol. 30, No. 5, pp. 102–107, September–October, 1989.
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Karapetyan, A.A., Struchkov, Y.T., Martirosyan, V.O. et al. Structure of 4-anilinopiperidine analgesics. I. The structure of the 2:1 solvate of 1(e)-(2-phenethyl)-2(e),5(a)-dimethyl-4(e)-(N-propionylanilino)-piperidine bisulfate monohydrate with cyclohexanone. J Struct Chem 30, 782–787 (1989). https://doi.org/10.1007/BF00763802
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DOI: https://doi.org/10.1007/BF00763802