4-(5-((1E,3E)-4-(benzo[d][1,3]dioxol-5-yl)buta-1,3-dien-1-yl)-1,3,4-oxadiazol-2-yl)aniline

Abstract

This research aimed to develop a new semisynthetic piperine compound derived from black pepper (Piper nigrum, Piperaceae), commonly known as “King of Spices”. Piperine was isolated from the ethanolic extract of Piper nigrum by the Soxhlet extraction method. In this, 5(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (Piperine) is used as a starting material to form (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoic acid (2). After that, ethyl (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate (3) will be formed by the esterification process. The (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienehydrazide (4) was formed by using hydrazine and ethanol. In the final step, the hydrazide was reacted with p-aminobenzoic acid to form 4-(5-((1E,3E)-4-(benzo[d][1,3]dioxol-5-yl)buta-1,3-dien-1-yl)-1,3,4-oxadiazol-2-yl)aniline (5). The novel synthesized compound was characterized by IR, 1H NMR, 13C NMR, and mass spectroscopy.