Electrochemical synthesis of the new substituted phenylpiperazines

• Published in: Journal of electroanalytical chemistry (Lausanne, Switzerland) Vol. 651; no. 1; pp. 72 - 79
• Main Authors: Nematollahi, Davood, Amani, Amene
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier B.V 2011; Elsevier
• Subjects: acids; aqueous solutions; Arylsulfinic acid; carbon; Chemistry; Cyclic voltammetry; Electrochemical synthesis; Electrochemistry; electrodes; Exact sciences and technology; General and physical chemistry; Green chemistry; Kinetics and mechanism of reactions; oxidation; Phenylpiperazine; wastes; Cyclic voltammetry; Green chemistry; Phenylpiperazine; Arylsulfinic acid; Electrochemical synthesis; Michael addition; Sulfone; Sulfinic acid; Wasteless technology; Carbon; Electrodes; EC mechanism; Oxidation; Piperazine derivatives; Aqueous solution; Electrochemical reaction; Chemical synthesis; Organic compounds; Glassy state
• ISSN: 1572-6657; 1873-2569
• DOI: 10.1016/j.jelechem.2010.10.024

Electrochemical oxidation of 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone ( 1) has been studied in the presence of arylsulfinic acids ( 3a–c) as nucleophiles in aqueous solutions using cyclic voltammetry and controlled-potential coulometry methods. The results revealed that quinone-imine derived from oxidation of 1 participates in Michael type addition reaction with 3a–c and via an EC mechanism converts to the corresponding new phenylpiperazine derivatives. The present work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for synthesis of some new phenylpiperazine derivatives in aqueous solutions with high atom economy and safe waste under ambient conditions and in an undivided cell using a carbon electrode.