Rel -4-[(3R ,5S )-3,5-dimethyl-1-piperazinyl]-Benzenamine
[CAS# 1033330-43-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: Rel -4-[(3R ,5S )-3,5-dimethyl-1-piperazinyl]-Benzenamine
• Synonyms: 4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]aniline
• Molecular Formula: C₁₂H₁₉N₃
• Molecular Weight: 205.30
• CAS Registry Number: 1033330-43-6
• SMILES: C[C@@H]1CN(C[C@@H](N1)C)C2=CC=C(C=C2)N

Properties

• Solubility: Soluble (41 g/L) (25 °C), Calc.^*
• Density: 1.026±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.547, Calc.^*
• Boiling Point: 381.5±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 184.6±23.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Rel-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-benzenamine is a synthetic compound recognized for its potential in pharmaceutical and chemical research. It belongs to the class of substituted piperazines, which have a broad range of biological activities due to their ability to bind to various receptors and enzymes. The discovery of this molecule emerged from investigations into piperazine derivatives as potential candidates for neurological and antimicrobial treatments.

The piperazine moiety, which is central to the structure of rel-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-benzenamine, is known for its versatility in drug design. The stereochemistry, particularly the (3R,5S) configuration, plays a crucial role in the molecule’s bioactivity and receptor selectivity. The two methyl groups at the 3- and 5-positions influence the molecule's three-dimensional shape and can enhance its interaction with biological targets by providing steric effects that optimize binding affinity. The benzenamine group provides aromatic character, contributing to potential interactions through π-π stacking or hydrogen bonding.

One major application of rel-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-benzenamine is in the development of pharmaceutical agents targeting the central nervous system. Piperazine derivatives have shown promise as dopamine and serotonin receptor modulators, which are relevant in treating conditions such as depression, anxiety, and schizophrenia. The specific substitution pattern in this molecule allows researchers to explore its selectivity for different receptor subtypes, optimizing therapeutic effects while minimizing side effects.

Additionally, this compound can serve as a building block in synthetic chemistry. The presence of both aromatic and piperazinyl groups makes it a useful intermediate in the synthesis of more complex molecules, including potential antimicrobial agents. Piperazine derivatives have demonstrated activity against various bacterial strains, suggesting that rel-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-benzenamine might contribute to the discovery of new antibiotics or antimicrobial agents effective against resistant pathogens.

Research into this compound also extends to material science. Substituted piperazines are being explored for their potential as ligands in coordination chemistry, where they form complexes with metals for catalysis or imaging applications. The structural properties of rel-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-benzenamine make it suitable for further modifications that can enhance its functional utility.

The discovery and application of rel-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-benzenamine underscore its importance in medicinal chemistry and synthetic design. Its versatile structure enables applications across multiple research fields, contributing to advancements in drug discovery and chemical synthesis.

References

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