230615-70-0 | 7,8,9,10-Tetrahydro-8-(trifluoroacetyl)-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine (N-(Trifluoroacetyl)varenicline)

CAS:230615-70-0 | 7,8,9,10-Tetrahydro-8-(trifluoroacetyl)-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine (N-(Trifluoroacetyl)varenicline),Description

This compound, also known as 2,2,2-trifluoro-1-(6,7,9,10-tetrahydro-8H-6,10-methanoazepino[4,5-g]quinoxalin-8-yl)ethan-1-one, has a molecular weight of 307.27. It is a solid at room temperature.

Synthesis Analysis

The synthesis of this compound involves the use of sodium hydroxide in toluene at 37-40°C. The reaction mixture is then treated with Darco KB-B, and the resulting solution is distilled with methanol. The product is then added to a L-(+)-tartaric acid/methanol solution to form a salt.

Molecular Structure Analysis

The InChI code for this compound is 1S/C15H12F3N3O/c16-15(17,18)14(22)21-6-8-3-9(7-21)11-5-13-12(4-10(8)11)19-1-2-20-13/h1-2,4-5,8-9H,3,6-7H2. This indicates the presence of 15 carbon atoms, 12 hydrogen atoms, 3 fluorine atoms, 3 nitrogen atoms, and 1 oxygen atom in the molecule.

Chemical Reactions Analysis

The compound undergoes a reaction with sodium hydroxide in toluene at 37-40°C. This reaction results in the conversion of the compound to varenicline.

Physical And Chemical Properties Analysis

This compound is a solid at room temperature. It has a molecular weight of 307.27. The InChI code for this compound is 1S/C15H12F3N3O/c16-15(17,18)14(22)21-6-8-3-9(7-21)11-5-13-12(4-10(8)11)19-1-2-20-13/h1-2,4-5,8-9H,3,6-7H2.

Scientific Research Applications

Corrosion Inhibition

Quinoxaline derivatives have been explored for their corrosion inhibition properties. Experimental and computational studies on propanone derivatives of quinoxaline have demonstrated their efficacy as inhibitors of mild steel corrosion in hydrochloric acid solutions. These compounds exhibit mixed-type inhibitive action, significantly reducing the rate of anodic and cathodic corrosion reactions. The adsorption of these molecules on the mild steel surface forms a protective layer, mitigating corrosion in acidic environments (Olasunkanmi & Ebenso, 2019).

Synthetic Chemistry and Drug Design

Quinoxaline derivatives play a crucial role in synthetic chemistry, serving as building blocks for the synthesis of complex molecules with potential therapeutic applications. Their synthesis and conformational analysis have contributed significantly to the development of novel compounds with diverse biological activities. These activities include efforts to create more effective molecules through the manipulation of quinoxaline structures, highlighting the compound's versatility and importance in drug design and development (Karkhut et al., 2014).

Antimycobacterial Agents

Quinoxaline derivatives have shown promise as antimycobacterial agents. A diversity-oriented synthesis approach has led to the development of substituted pyridines and dihydro-6H-quinolin-5-ones tethered with aryls and heteroaryls, demonstrating significant in vitro activity against Mycobacterium tuberculosis. This highlights the potential of quinoxaline derivatives in the treatment of tuberculosis and other bacterial infections (Kantevari et al., 2011).

Luminescence and Magnetic Properties

Quinoxaline derivatives have also found applications in materials science, particularly in the development of compounds with unique luminescence and magnetic properties. Lanthanide complexes based on quinoxaline derivatives exhibit photoluminescence and slow magnetization relaxation, suggesting applications in optical materials and magnetic storage devices (Chu et al., 2018).

Safety And Hazards

The compound is labeled with the GHS07 pictogram. The hazard statements associated with this compound are H302, H315, H319, H335. The precautionary statements are P261, P280, P301, P301, P302, P305, P312, P338, P351, P352.

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