Journal of Chemical Crystallography

, Volume 41, Issue 6, pp 868–873 | Cite as

Synthesis and Crystal Structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

  • Ambika Sambyal
  • R. K. Bamezai
  • T. K. Razdan
  • Vivek K. Gupta
Original Paper

Abstract

The title compound, (2S,6R), Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (C32H30N2O2), was synthesised by the reaction of benzaldehyde, aniline and ethylacetoacetate, in the presence of l (−) proline–Fe(III) complex, formed in situ, at room temperature. The compound was characterized by spectral methods and X-ray diffraction studies. The compound crystallizes in the triclinic space group P − 1 with the following unit-cell parameters: a = 9.651(4), b = 10.909(5), c = 13.737(7) Å, α = 106.597(7), β = 108.664(8), γ = 99.779(6)°, Z = 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at 100 K and refined by full-matrix least-squares procedures to a final R-value of 0.0633 for 3415 observed reflections. The 1,2,5,6-tetrahydropyridine ring exhibits a flat boat conformation. The structure has intra- and intermolecular hydrogen bonds of the type N–H···O, C–H···O and C–H···π, which help to stabilize the crystal structure.

Graphical Abstract

Crystal structure analysis of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate.

Keywords

Asymmetric synthesis Crystal structure Direct methods Hydrogen bonding C–H···π stacking interactions Chiral tetrahydropyridine 

Notes

Acknowledgments

The authors are thankful to Prof. P. K. Bharadwaj, Department of Chemistry, IIT, Kanpur, India, for the use of the data collection facility and to Dr. R.G.Bhat (IISER, Pune) for spectral analysis and HPLC.

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Ambika Sambyal
    • 1
  • R. K. Bamezai
    • 1
  • T. K. Razdan
    • 1
  • Vivek K. Gupta
    • 2
  1. 1.Department of ChemistryUniversity of JammuJammu TawiIndia
  2. 2.Department of PhysicsUniversity of JammuJammu TawiIndia

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