169458-69-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1,3-dibenzylpiperazine is used as a building block for the synthesis of various pharmaceuticals, particularly for the development of potential antipsychotic and anticonvulsant agents. Its unique structure and chirality contribute to the creation of novel and effective medications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (R)-1,3-dibenzylpiperazine is employed as a key component in the design and synthesis of enantiomerically pure drugs. Its chiral nature allows for the development of more targeted and safer therapeutic options, reducing side effects and improving patient outcomes.
Used in Anticancer Research:
(R)-1,3-dibenzylpiperazine has also been investigated for its potential anticancer properties. Its unique structure and interactions with biological targets make it a promising candidate for the development of novel cancer treatments, offering new avenues for research and therapeutic intervention.
Overall, (R)-1,3-dibenzylpiperazine is a versatile and valuable compound in the pharmaceutical and medicinal chemistry industries, with a wide range of applications and potential for further research and development.

Upstream product

• 100-46-9 benzylamine 
• 18942-49-9 Boc-D-Phe-OH 
• 174799-52-1 tert-butyl {2-[benzylamino]ethyl}carbamate 
• 100-52-7 benzaldehyde 
• 208840-35-1 1-Benzyl-3(R)-(benzyl)-piperazine-2,5-dione 
• 481038-73-7 C₂₅H₃₂N₂O₅ 

Downstream Products

• 1144508-53-1 (R)-(3-bromothiophen-2-yl)(2,4-dibenzylpiperazin-1-yl)methanone 
• 850037-77-3 C₁₉H₂₀N₂O 
• 1443434-06-7 C₂₀H₂₄N₂O₂ 
• 952568-42-2 (R)-2-(2-Bromophenoxy)-1-(2,4-dibenzylpiperazin-1-yl)ethanone 
• 952568-43-3 C₃₂H₃₃N₃O 
• 952568-40-0 C₂₇H₃₀N₂O 
• 481038-81-7 [(R)-3-((R)-2,4-Dibenzyl-piperazin-1-yl)-1-(2-fluoro-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 947278-69-5 C₃₅H₃₃N₃O 
• 481038-88-4 [(R)-3-((R)-2-Benzyl-4-carbamoylmethyl-piperazin-1-yl)-1-(2-fluoro-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Efficient one-pot synthesis of enantiomerically pure: N -protected-α-substituted piperazines from readily available α-amino acids

A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83-92%), starting from commercially available N-protected amino acids. The methodology represents an efficient and simple one-pot procedure, employing a synthetic sequence consisting of an Ugi-4 component reaction, a Boc-deprotection, an intramolecular cyclisation reaction and a final reduction (UDCR). From the benzyl protected precursors, the 2-substituted piperazines bearing a Boc-protecting group could consequently also be obtained via a simple protection and deprotection step of the corresponding piperazines. The practical utility of this methodology was demonstrated for chiral drug synthesis.

Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights to Realize the Enantioselective Synthesis of Piperazines

An efficient and practical catalytic approach for the enantioselective synthesis of 3-substituted morpholines through a tandem sequential one-pot reaction employing both hydroamination and asymmetric transfer hydrogenation reactions is described. Starting from ether-containing aminoalkyne substrates, a commercially available bis(amidate)bis(amido)Ti catalyst is utilized to yield a cyclic imine that is subsequently reduced using the Noyori-Ikariya catalyst, RuCl [(S,S)-Ts-DPEN] (η6-p-cymene), to afford chiral 3-substituted morpholines in good yield and enantiomeric excesses of >95%. A wide range of functional groups is tolerated. Substrate scope investigations suggest that hydrogen-bonding interactions between the oxygen in the backbone of the ether-containing substrate and the [(S,S)-Ts-DPEN] ligand of the Ru catalyst are crucial for obtaining high ee's. This insight led to a mechanistic proposal that predicts the observed absolute stereochemistry. Most importantly, this mechanistic insight allowed for the extension of this strategy to include N as an alternative hydrogen bond acceptor that could be incorporated into the substrate. Thus, the catalytic, enantioselective synthesis of 3-substituted piperazines is also demonstrated.

Synthesis and SAR of potent and selective tetrahydropyrazinoisoquinolinone 5-HT2C receptor agonists

The 5-HT2C receptor has been implicated as a critical regulator of appetite. Small molecule activation of the 5-HT2C receptor has been shown to affect food intake and regulate body weight gain in rodent models and more recently in hu

Piperazine derivatives

A piperazine compound of the formula: STR1 wherein: X is carbonyl or sulfonyl; Y is a direct bond or lower alkylene; and R1, R2, R3, R4 are as defined herein. The compounds are advantageously used as Tachykinin antagonists in the treatment of respiratory diseases, ophthalmic diseases and inflammatory diseases, for example.