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
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.
KeywordsAmide Benzene Ring Unit Cell Parameter Monohydrate Piperidine
Unable to display preview. Download preview PDF.
- 1.S. A. Vartanyan, R. S. Vartanyan, V. N. Zhamagortsyan, et al., USSR Inventor's Certificate S07 D 295/04//A61 K 31/44, “1-(2-Phenethyl)-4-N-propionylanilinopiperidine and its salts having analgesic action and a means for their preparation,” Publ. November 30, 1985; Byul. Izobr., No. 44, 271 (1985).Google Scholar
- 2.R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya,28, No. 5, 1029–1030 (1983).Google Scholar
- 3.O. M. Peeters, N. M. Blaton, C. J. De Ranter, et al., J. Cryst. Mol. Struct.,9, No. 3, 153–161 (1979).Google Scholar
- 4.O. M. Peeters, N. M. Blaton, and C. J. De Ranter, Acta Crystallogr.,B35, No. 4, 999–1001 (1979).Google Scholar
- 5.M. H. J. Koch, C. J. De Ranter, M. Rolies, and O. Didberg, Acta Crystallogr.B32 No. 8, 2529–2531 (1976).Google Scholar
- 6.L. Gylbert and D. Carlstrom, Acta Crystallogr.,B33, No. 9, 2833–2837 (1977).Google Scholar