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Journal of Chemical Crystallography

, Volume 47, Issue 5, pp 166–172 | Cite as

Structure Determination of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)-2-[4-(dimethylamino)phenyl]acetonitrile, an α-Amino Nitrile Obtained by a Modified Strecker Reaction

  • Aurora L. Carreño Otero
  • José H. Quintana
  • José Antonio Henao
  • Vladimir V. Kouznetsov
  • José Miguel Delgado
  • Graciela Díaz de Delgado
Original Paper

Abstract

Modified Strecker synthesis between 4-(dimethylamino)benzaldehyde (1), 1,2,3,4-tetrahydroisoquinoline (2), and potassium cyanide in the presence of silica-supported sulfuric acid in MeCN at room temperature produced the new compound 2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-[4-(dimethylamino)phenyl]acetonitrile (3). The yellow prisms obtained from petroleum ether:ethyl acetate (30:1) mixture at 25 °C are monoclinic, space group P21/c, with a = 13.2197(9) Å, b = 6.4454(4) Å, c = 19.1092(13) Å, β = 95.051(8)°, V = 1621.90(19) Å3, Z = 4. The refinement converged to R = 0.0434, wR 2  = 0.1247, S = 1.02. Molecules of 3 interact via C–H⋯N and C–H⋯π contacts to form zig-zag ribbons that run along the a-axis and stack along the c-axis, connected by van der Waals interactions.

Graphical Abstract

Zig-zag ribbons connected by C–H⋯N and C–H⋯π interactions dominate the structure of the new α-amino nitrile 2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-[4-(dimethylamino)phenyl]acetonitrile synthesized by a one-pot Strecker reaction.

Keywords

α-Amino nitriles Multi-component reactions (MCRs) Three component Strecker reaction Girgensohnine analogues 

Notes

Acknowledgements

The authors thank Vicerrectoría de Investigación y Extensión, Universidad Industrial de Santander (UIS) and Laboratorio de Rayos-X-Parque Tecnológico Guatiguará, UIS, Piedecuesta, Santander, Colombia, for the support to the diffraction data acquisition facilities. Financial support from Departamento Administrativo de Ciencia, Tecnología e Innovación de Colombia, COLCIENCIAS, RC-Contract 624-2014, is gratefully acknowledged. A.L.C.O. thanks COLCIENCIAS for the fellowship No. 567/2012 to carry out Doctoral studies.

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Aurora L. Carreño Otero
    • 1
  • José H. Quintana
    • 2
    • 4
  • José Antonio Henao
    • 2
    • 4
  • Vladimir V. Kouznetsov
    • 1
  • José Miguel Delgado
    • 3
    • 4
  • Graciela Díaz de Delgado
    • 3
    • 4
  1. 1.Laboratorio de Química Orgánica y Biomolecular, Escuela de QuímicaUniversidad Industrial de SantanderBucaramanga A.A. 678Colombia
  2. 2.Grupo de Investigación en Química Estructural (GIQUE), Escuela de QuímicaUniversidad Industrial de SantanderBucaramanga A.A. 678Colombia
  3. 3.Laboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de CienciasUniversidad de Los AndesMéridaVenezuela
  4. 4.Red Suramericana de Caracterización Estructural de Farmacóforos, Catalizadores y SemiconductoresUniversidad Industrial de SantanderBucaramanga A.A. 678Colombia

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