Iminopyrrolyl ligands have attracted an attention in the field of coordination chemistry. As every iminopyrrolyl ligand contains at least one acidic pyrrole NH group, it often forms an anionic five-membered chelate ring with a metal. Unlike the familiar pincer framework ligand systems, iminopyrrolyl coordination chemistry is in a developing stage. Hence, we set the synthesis of bis(iminopyrrole) framework ligand containing the piperazine ring as a spacer unit between two mono(iminopyrrolyl) moieties. The Mannich reaction of pyrrole-2-carbaldehyde with piperazine and formaldehyde afforded two new dialdehydes: N,N′-bis(5-formylpyrrol-1-ylmethyl)piperazine 1 and N,N′-bis(5-formylpyrrol-2-ylmethyl)piperazine, 2, which are regioselective products formed in good yields. The pyrrole N aminomethylated dialdehyde 1 was isolated in the absence of an added acid. Conversely, the pyrrole α-C aminomethylated dialdehyde compound 2 was obtained in the presence of a mineral acid. They have different spectroscopic and physical properties. Even they offered different Schiff bases under the same reaction conditions. The Schiff base condensation reaction of 2 with 2,6-diisopropylanilline in the presence of HNO3 gave the expected [1+2] Schiff base in 53% yield after column separation. Conversely, the other dialdehyde 1 yielded the piperazinylmethyl C–N bonds hydrolyzed known 2-iminopyrrole compound. Further, the treatment of the structurally characterized [1+2] bis(iminopyrrolyl) ligand with copper(II) carboxylates [Cu(OOCR)2(H2O)] (R=H, Me and Ph) gave three different binuclear five-coordinate copper(II) complexes. Their structures were determined by single crystal X-ray diffraction studies. Interestingly, the piperazine ring nitrogens are not coordinated, rather involved in intramolecular hydrogen bonding interactions with the coordinated solvent molecules at the copper atom.