tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (CAS 571188-59-5): A Comprehensive Introduction
tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, with the CAS number 571188-59-5, is a significant organic compound in the field of chemical research and pharmaceutical development. This compound has attracted considerable attention due to its unique chemical structure and potential applications. In this article, we will delve into various aspects of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, including its properties, uses, applications in different fields, and preparation methods.
Properties of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is an organic solid at room temperature. Its chemical formula is \(C_{14}H_{22}N_{4}O_{2}\), and it has a molecular weight of approximately 278.35 g/mol. The compound contains a piperazine ring and a pyridine ring, which are common structural motifs in many bioactive molecules. The tert-butyl group attached to the carboxylate moiety provides steric hindrance and affects the compound’s reactivity and solubility.
Regarding its solubility, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is sparingly soluble in water but shows good solubility in common organic solvents such as dichloromethane, chloroform, and dimethyl sulfoxide (DMSO). This solubility property is important for its use in chemical reactions and biological assays.
The melting point of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is typically in the range of [specific melting point range if available]. This physical property can be used for its identification and purification during the synthesis process.
Uses of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
One of the primary uses of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate is as an intermediate in the synthesis of various pharmaceutical compounds. The presence of the amino group on the pyridine ring and the reactive piperazine moiety makes it a valuable building block for the construction of more complex molecules with potential biological activities.
In drug discovery, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate can be used to introduce specific structural features into drug candidates. For example, it can be used to modify the pharmacokinetic and pharmacodynamic properties of a drug by altering its binding affinity to target proteins, improving its solubility, or enhancing its metabolic stability.
Another use of this compound is in the field of chemical research. It can be used as a starting material for the synthesis of novel organic compounds with unique chemical and physical properties. Researchers can explore different reaction conditions and synthetic routes to prepare derivatives of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate and study their potential applications in areas such as materials science and catalysis.
Applications in Different Fields
Pharmaceutical Industry
In the pharmaceutical industry, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate has shown great potential in the development of drugs for various diseases. For example, it can be used in the synthesis of drugs targeting the central nervous system. The piperazine and pyridine moieties in the compound can interact with specific receptors in the brain, leading to potential therapeutic effects such as anti-depressant, anti-anxiety, or anti-psychotic activities.
It can also be used in the development of anti-cancer drugs. The compound can be incorporated into drug molecules to target specific cancer-related proteins or pathways. By modifying the structure of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, researchers can design drugs with improved selectivity and efficacy against cancer cells while minimizing side effects on normal cells.
Chemical Research
In chemical research, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate can be used as a ligand in coordination chemistry. The nitrogen atoms in the piperazine and pyridine rings can coordinate with metal ions, forming stable metal complexes. These complexes can be used as catalysts in various organic reactions, such as cross-coupling reactions, oxidation reactions, and reduction reactions.
It can also be used in the synthesis of functional materials. For example, by incorporating tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate into polymers or dendrimers, researchers can prepare materials with unique optical, electrical, or magnetic properties. These materials can have potential applications in areas such as sensors, displays, and energy storage.
Preparation Methods of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
There are several methods for the preparation of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate. One common method involves the reaction between 6-aminopyridin-3-ylamine and tert-butyl 1-piperazinecarboxylate. This reaction is typically carried out in the presence of a suitable solvent and a catalyst. The reaction conditions, such as temperature, reaction time, and the ratio of reactants, need to be carefully controlled to ensure a high yield of the desired product.
Another method involves a multi-step synthesis. First, a suitable pyridine derivative is prepared, which is then reacted with a piperazine derivative to form the intermediate. Finally, the intermediate is reacted with a tert-butyl protecting group reagent to introduce the tert-butyl carboxylate group. This multi-step approach allows for more flexibility in the synthesis and can be used to prepare derivatives of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate with different substituents.
During the preparation process, purification steps are usually required to obtain a pure product. Common purification methods include recrystallization, column chromatography, and distillation. These methods can remove impurities and by-products from the reaction mixture, ensuring the quality of the final product.
Send InquiryReferences
- [Reference 1 Name] https://example.com/reference1
- [Reference 2 Name] https://example.com/reference2