1034-11-3

Basic information

• Product Name: 1,4-Dibenzylpiperazine
• Synonyms: 1,4-Dibenzylpiperazin; 1,4-Dibenzylpipérazine; Piperazine, 1,4-bis(phenylmethyl)-
• CAS NO: 1034-11-3
• Molecular Formula: C₁₈H₂₂N₂
• Molecular Weight: 266.3807
• Mol File: 1034-11-3.mol

Chemical Properties

• Boiling Point: 376.9°C at 760 mmHg
• Flash Point: 166.4°C
• Density: 1.086g/cm³
• Vapor Pressure: 7.03E-06mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: 1,4-Dibenzylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dibenzylpiperazine(1034-11-3)
• EPA Substance Registry System: 1,4-Dibenzylpiperazine(1034-11-3)

Safety Data

• Hazardous Substances Data: 1034-11-3(Hazardous Substances Data)

Upstream product

• 110-85-0 piperazine 
• 100-52-7 benzaldehyde 
• 100-44-7 benzyl chloride 
• 106-93-4 ethylene dibromide 
• 140-28-3 N,N'-Dibenzylethylenediamine 
• 84609-66-5 3-benzylcyclohexanospiro-2-oxazolidine 
• 107-21-1 ethylene glycol 
• 100-46-9 benzylamine 
• 124782-15-6 2,4,6,8,10,12-hexabenzyl-2,4,5,8,10,12-hexaazatetracyclo[5.5.0.0^3,11.0^5,9]dodecane 
• 65950-40-5 N,N-bis(tosylmethyl)benzylamine 
• 1074-42-6 1-benzylaziridine 
• 123-91-1 1,4-dioxane 
• 854838-60-1 1,4-bis-(2,2-bis-ethoxycarbonyl-1-phenyl-ethyl)-piperazine 
• 2759-28-6 1-phenylmethylpiperazine 

Downstream Products

• 10507-25-2 N,N'-dibenzyl-N,N'-1,2-ethanediylbisformamide 
• 77917-07-8 N,N'-dibenzyl-2,3-diketopiperazine 
• 110-85-0 piperazine 
• 768387-56-0 di(prop-2-ynyl) piperazine-1,4-dicarboxylate 

Relevant articles and documents

Oxidation of N-benzyl aziridine by molecular iodine: Competition of electron transfer and heterolytic pathways

Excess N-benzyl aziridine (1) reacts with I2 to afford dimer 2, tetramer 3, benzaldehyde (4), and iodoamine 5. The reaction is interpreted as occurring by both electron transfer (ET) and heterolytic mechanisms. An ET mechanism is substantiated

1,4-Dibenzylpiperazines possess anticocaine activity

N,N-Dibenzylpiperazines have high affinity for sigma receptors, and we aimed to increase their anticocaine activity by introducing substituents known to enhance such activity in other sigma ligands. Ligands with high affinity for sigma-1 receptors resulte

Ruthenium Complex Catalyzed N-Heterocyclization. Indoles from Aminoarenes and Glycols.

N-Methylaniline reacted with ethylene glycol in the presence of a homogenous ruthenium catalyst (1 molpercent based on ethylene glycol) to give 1-methylindole in 51percent yield.Similarly, aniline reacted with 2,3-butanediol affording 2,3-dimethylindole in 58percent yield.The yields of indoles were affected by the molar ratio of aminoarene to glycol.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Nickel-Catalyzed Regio- And Stereospecific C-H Coupling of Benzamides with Aziridines

A nickel-catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with aryl- and alkyl-substituted aziridines has been disclosed. The current strategy provides direct access to benzolactams by the C-H alkylation-intramolecular amidation cascade event with the concomitant removal of the aminoquinoline auxiliary. The regioselectivity of ring opening of aziridines can be controlled by the substituents. The reaction with chiral aziridines proceeds with inversion of configuration, thus suggesting an SN2-type nucleophilic ring-opening pathway.

A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles

An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.

Selective, Catalytic, and Dual C(sp3)-H Oxidation of Piperazines and Morpholines under Transition-Metal-Free Conditions

By using cheap and innocuous reagents, such as NaClO2, NaOCl, and catalytic amounts of TEMPO, a new environmentally friendly protocol for the selective and catalytic TEMPO C(sp3)-H oxidation of piperazines and morpholines to 2,3-diketopiperazines (2,3-DKP) and 3-morpholinones (3-MPs), respectively, has been developed. This novel direct access to 2,3-DKP from piperazines provides significant advantages over the traditional N-monoacylation/intramolecular C-N cyclization procedure. Additionally, by modulating the amounts of TEMPO, 2-alkoxyamino-3-morpholinone can be prepared from morpholine derivatives, which would enable further functionalization at the C2 position of the morpholine skeleton.

RuO4-mediated oxidation of N-benzylated tertiary amines. Four- And three-membered azacycloalkanes as substrates

Similarly to N-benzylpiperidine and -pyrrolidine, N-benzylazetidine underwent RuO4-catalyzed oxidation by attack at both types of N-methylene C-H bonds: Endocyclic and exocyclic (benzylic). If the reaction is performed in the presence of cyanide, α-aminon

Method for producing N-alkylpiperazine

PROBLEM TO BE SOLVED: To provide a method for producing N-alkyl piperazines in high yield by selectively alkylating one amino group.SOLUTION: In the method for producing N-alkyl piperazines, piperazines represented by general formula (1) are reacted with a specific alkylating agent in the presence of an acid. In the formula: R-Rare each independently a hydrogen atom, a methyl group, an ethyl group, a 3-8C linear alkyl group or the like, a hydroxyethyl group, a hydroxypropyl group, a dihydroxypropyl group, a methoxy group, an ethoxy group, a phenyl group, a benzyl group, a 2-phenylethyl group, or the like.

Novel bis-arylalkylamines as myeloperoxidase inhibitors: Design, synthesis, and structure-activity relationship study

Human myeloperoxidase (MPO) plays an important role in innate immunity but also aggravates tissue damage by oxidation of biomolecules at sites of inflammation. As a result from a recent high-throughput virtual screening approach for MPO inhibitors, bis-2,2′-[(dihydro-1,3(2H,4H) pyrimidinediyl)bis(methylene)]phenol was detected as a promising lead compound for inhibition of the MPO-typical two-electron oxidation of chloride to hypochlorous acid (IC50= 0.5 μM). In the present pharmacomodulation study, 37 derivatives of this lead compound were designed and synthesized driven by comprehensive docking studies and the impact on the chlorination activity of MPO. We describe the structural requirements for optimum (i) binding to the heme periphery and (ii) inhibition capacity. Finally, the best three inhibitors (bis-arylalkylamine derivatives) were probed for interaction with the MPO redox intermediates Compound I and Compound II. Determined apparent bimolecular rate constants together with determination of reduction potential and nucleophilicity of the selected compounds allowed us to propose a mechanism of inhibition. The best inhibitor was found to promote the accumulation of inactive form of MPO-Compound II and has IC50= 54 nM, demonstrating the successful approach of the drug design. Due to the similarity of ligand interactions between MPO and serotonine transporter, the selectivity of this inhibitor was also tested on the serotonin transporter providing a selectivity index of 14 (KiSERT/IC50MPO).