The molecular design of two molecules have been derived from the tailoring of the benzodiazepine moiety in which the amide group is in cyclic form as well as bioisosteric (CH2≈NH) and we have incorporated the same amide linkage in open chain by keeping the triazolo-pyrrole ring having Mannich base of urea/thiourea linkage with piperidine nucleus for CNS depression activity. Phenyl substituted 5-pyrazolone has been synthesized by the reaction between phenyl hydrazine and ethyl acetoacetate and substituted trizolo-pyrrole fused ring has been synthesized by condensation of benzoylated phenyl substituted 5-pyrazolone with urea. This on reaction between Mannich base which has been synthesized by the reaction between benzaldehyde with piperidine and urea/thiourea produced amide bridge having variable atom X=O: Urea and X=S: Thiourea. The two components were characterized for their structural confirmation by IR spectra and elemental microanalysis