Journal of Structural Chemistry

, Volume 30, Issue 5, pp 782–787 | Cite as

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

  • A. A. Karapetyan
  • Yu. T. Struchkov
  • V. O. Martirosyan
  • R. S. Vartanyan
  • S. A. Vartanyan
Article

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.

Keywords

Amide Benzene Ring Unit Cell Parameter Monohydrate Piperidine 

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Literature Cited

  1. 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. 2.
    R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya,28, No. 5, 1029–1030 (1983).Google Scholar
  3. 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. 4.
    O. M. Peeters, N. M. Blaton, and C. J. De Ranter, Acta Crystallogr.,B35, No. 4, 999–1001 (1979).Google Scholar
  5. 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. 6.
    L. Gylbert and D. Carlstrom, Acta Crystallogr.,B33, No. 9, 2833–2837 (1977).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • A. A. Karapetyan
  • Yu. T. Struchkov
  • V. O. Martirosyan
  • R. S. Vartanyan
  • S. A. Vartanyan

There are no affiliations available

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