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


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.

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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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Correspondence to Graciela Díaz de Delgado.

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Carreño Otero, A.L., Quintana, J.H., Henao, J.A. et al. 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. J Chem Crystallogr 47, 166–172 (2017).

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