By the interaction of 2-aminoacetophenone 1 with aromatic aldehydes (2E)-1-(2aminophenyl)-3-phenylprop-2-en-1-ones 2-8 were synthesized. Their interaction with glycine chloride hydrochloride results the 5-[(E) -2-arylvinyl]-1,2-dihydro-3H-1,4-benzodiazepin-2-ones 915. For the first time a series of (3Z)-3-arylidene(hetarylidene)-5-[(E)-2-aryl(hetaryl)vinyl]-1,2dihydro-3H-1,4-benzodi-azepin-2-ones 16-22 was prepared in the reaction of 9-15 with aromatic aldehydes. The 3(Z)-3-benzylidene-5-[(E)-2-arylvinyl]-1,2-dihydro-3H-1,4-benzodiazepin-2-one 16  was synthesized by the counter-synthesis method by reacting 5-methy-l-1,4-benzodiazepin-2-one  with benzaldehyde. The crystals of target compounds 16 crystalizes in monoclinic space group P21/c with unit cell parameters a = 12.604(1) b = 17.444(2) c = 8.448(1)Å, β = 97.172(10)º and 20 in trigonal space group R-3 with parameters a = b = 51.364(3), c 4.045(1) Å. The crystal structures of both compounds reveal the formation of centrocymmetric dimer due to hydrogen bonds N1-H···O2 = 2.874 and 2.917 Å for 16 and 20, respectively. The crystal packing in the structure 20 reveals the formation of infinite channels along c axis of the crystal filled with the disordered DMF solvent molecules. Compound 20 exhibit promising analgesic activity