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

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) A, b = 6.4454(4) A, c = 19.1092(13) A, β = 95.051(8)°, V = 1621.90(19) A3, 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. 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.