Cas no 162240-95-1 ((3S,5S)-1-benzyl-3,5-dimethylpiperazine)

(3S,5S)-1-Benzyl-3,5-dimethylpiperazine is a chiral piperazine derivative characterized by its stereospecific configuration at the 3 and 5 positions. This compound serves as a valuable intermediate in pharmaceutical synthesis, particularly in the development of enantioselective drugs due to its rigid, well-defined stereochemistry. The benzyl group enhances solubility in organic solvents, facilitating further functionalization, while the dimethyl substitution imparts steric control in reactions. Its high purity and consistent stereochemical integrity make it suitable for applications in asymmetric catalysis and medicinal chemistry research. The compound’s stability under standard conditions ensures reliable performance in synthetic workflows.
(3S,5S)-1-benzyl-3,5-dimethylpiperazine structure
162240-95-1 structure
Product Name:(3S,5S)-1-benzyl-3,5-dimethylpiperazine
CAS No:162240-95-1
MF:C13H20N2
MW:204.311303138733
MDL:MFCD11973744
CID:832244
PubChem ID:10943605
Update Time:2025-11-02

(3S,5S)-1-benzyl-3,5-dimethylpiperazine Chemical and Physical Properties

Names and Identifiers

    • Piperazine, 3,5-diMethyl-1-(phenylMethyl)-, (3S-trans)- (9CI)
    • (3S,5S)-1-Benzyl-3,5-dimethylpiperazine
    • LogP
    • (3S, 5S)-cis-1-Benzyl-3,5-dimethyl-piperazine
    • (3S, 5S)-1-Benzyl-3,5-dimethyl-piperazine
    • HTDQGGNOPNSEKT-RYUDHWBXSA-N
    • SCHEMBL4279682
    • 162240-95-1
    • F87827
    • AKOS025296365
    • (3S,5S)-1-benzyl-3,5-dimethylpiperazine
    • MDL: MFCD11973744
    • Inchi: 1S/C13H20N2/c1-11-8-15(9-12(2)14-11)10-13-6-4-3-5-7-13/h3-7,11-12,14H,8-10H2,1-2H3/t11-,12-/m0/s1
    • InChI Key: HTDQGGNOPNSEKT-RYUDHWBXSA-N
    • SMILES: N1(CC2C=CC=CC=2)C[C@H](C)N[C@@H](C)C1

Computed Properties

  • Exact Mass: 204.1628
  • Monoisotopic Mass: 204.162648646g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 177
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2
  • Topological Polar Surface Area: 15.3?2

Experimental Properties

  • PSA: 15.27

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Additional information on (3S,5S)-1-benzyl-3,5-dimethylpiperazine

Comprehensive Overview of (3S,5S)-1-benzyl-3,5-dimethylpiperazine (CAS No. 162240-95-1)

The compound (3S,5S)-1-benzyl-3,5-dimethylpiperazine (CAS No. 162240-95-1) is a chiral piperazine derivative that has garnered significant attention in pharmaceutical and chemical research due to its unique structural properties and potential applications. This article delves into the chemical characteristics, synthesis methods, applications, and market trends of this compound, while also addressing frequently asked questions and recent developments in the field.

(3S,5S)-1-benzyl-3,5-dimethylpiperazine belongs to the class of piperazine derivatives, which are widely recognized for their versatility in drug design and organic synthesis. The presence of a benzyl group and two methyl substituents at the 3 and 5 positions of the piperazine ring confers distinct stereochemical and electronic properties to this molecule. Researchers often explore such chiral building blocks for their ability to influence the biological activity and pharmacokinetics of potential drug candidates.

One of the key features of (3S,5S)-1-benzyl-3,5-dimethylpiperazine is its stereochemistry. The (3S,5S) configuration makes it a valuable intermediate in the synthesis of enantiomerically pure compounds, particularly in the development of central nervous system (CNS) drugs and enzyme inhibitors. Recent studies have highlighted its utility in creating asymmetric catalysts and ligands for transition metal complexes, which are crucial in modern synthetic chemistry.

The synthesis of (3S,5S)-1-benzyl-3,5-dimethylpiperazine typically involves multi-step organic reactions, starting from readily available precursors. Common methods include the reductive amination of appropriate ketones or the alkylation of piperazine derivatives. Advanced techniques such as chiral resolution or enantioselective synthesis are often employed to achieve the desired stereochemical purity. These synthetic approaches are continuously optimized to improve yield and reduce environmental impact, aligning with the growing demand for green chemistry practices.

In pharmaceutical research, (3S,5S)-1-benzyl-3,5-dimethylpiperazine serves as a critical intermediate for the development of novel therapeutic agents. Its structural motif is found in several bioactive molecules targeting G-protein coupled receptors (GPCRs) and neurotransmitter systems. Recent publications have explored its incorporation into potential treatments for neurological disorders, making it a compound of interest in the context of drug discovery and precision medicine.

The market for (3S,5S)-1-benzyl-3,5-dimethylpiperazine is influenced by trends in pharmaceutical innovation and the increasing demand for chiral intermediates. As the industry shifts toward personalized therapies and targeted drug delivery systems, the need for high-purity stereochemical compounds like this one is expected to rise. Suppliers and manufacturers are focusing on scalable production methods to meet the demands of both academic and industrial researchers.

Frequently asked questions about (3S,5S)-1-benzyl-3,5-dimethylpiperazine include inquiries about its solubility, stability under various conditions, and handling precautions. Researchers also often seek information on its spectroscopic data (NMR, IR, MS) and regulatory status in different regions. These queries reflect the compound's relevance in both laboratory and industrial settings.

In conclusion, (3S,5S)-1-benzyl-3,5-dimethylpiperazine (CAS No. 162240-95-1) represents a valuable tool in modern chemistry and drug development. Its unique stereochemical properties and versatile applications make it a subject of ongoing research and commercial interest. As scientific advancements continue to uncover new uses for chiral piperazine derivatives, this compound is poised to remain at the forefront of medicinal chemistry and organic synthesis innovations.

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