5368-34-3

Usage

Chemical class

Piperazine

Physical state

White crystalline solid

Molecular weight

366.5 g/mol

Pharmaceutical use

Precursor in the synthesis of various pharmaceutical drugs

Industrial use

Building block in the production of other organic compounds

Biological activity

Central nervous system stimulant

Pharmacological potential

Anti-tumor agent

Research status

Ongoing investigations to fully understand its potential uses and effects

Upstream product

• 107-21-1 ethylene glycol 
• 79869-74-2 C₂₂H₂₄N₂ 
• 100-42-5 styrene 
• 140-28-3 N,N'-Dibenzylethylenediamine 

Downstream Products

• 5271-26-1 m-phenylpiperazine 

Relevant academic research and scientific papers

A simple one-pot method for the mercuric oxide mediated synthesis of piperazines via oxidative diamination of olefins

Mercuric oxide mediated one-pot synthesis of substituted piperazines via oxidative diamination of olefins with N-protected ethylene diamine has been reported. Among the various conditions tried, mercuric(II)oxide/tetrafluoroboric acid gave good to excellent yields of the desired products. A series of piperazines have been synthesized and characterized by NMR and mass spectroscopy methods.

Iridium-catalyzed condensation of amines and vicinal diols to substituted piperazines

A straightforward procedure is described for the synthesis of piperazines from amines and 1,2-diols. The heterocyclization is catalyzed by [Cp*IrCl2]2 and sodium hydrogen carbonate and can be achieved with either toluene or water as solvent. The transformation does not require any stoichiometric additives and only produces water as the byproduct. The reaction can be performed between a 1,2-diamine and a 1,2-diol or by a double condensation between a primary alkylamine and a 1,2-diol. At least one substituent is required on the piperazine ring to achieve the cyclization in good yield. The mechanism is believed to involve dehydrogenation of the 1,2-diol to the α-hydroxy aldehyde, which condenses with the amine to form the α-hydroxy imine. The latter rearranges to the corresponding α-amino carbonyl compound, which then reacts with another amine followed by reduction of the resulting imine. Piperazines are prepared by [Cp*IrCl 2]2-catalyzed heterocyclization of 1,2-diols with either 1,2-diamines or primary alkylamines. The reaction is performed in toluene or water and requires no stoichiometric additive. The key step in the mechanism is believed to be the isomerization of an α-hydroxy imine to the corresponding α-amino carbonyl compound. Copyright

Iridium catalysed synthesis of piperazines from diols

A green and atom-economical method has been developed for the synthesis of piperazines by cyclocondensation of diols and amines in aqueous media in the presence of a catalytic amount of [Cp*IrCl2]2. The Royal Society of Chemistry.