2-[(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine
[CAS# 122368-54-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: 2-[(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine
• Molecular Formula: C₁₇H₁₉ClN₂O
• Molecular Weight: 302.80
• CAS Registry Number: 122368-54-1
• EC Number: 696-012-4
• SMILES: C1CNCCC1OC(C2=CC=C(C=C2)Cl)C3=CC=CC=N3

Properties

• Density: 1.21±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.601, Calc.^*
• Boiling Point: 421.7±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 208.8±28.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

2-[(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine is an organic compound that has garnered interest due to its potential applications in medicinal chemistry and as a pharmacological agent. The structure of this compound consists of a pyridine ring, which is a common structural motif in a variety of bioactive molecules, and two key functional groups attached to it: a 4-chlorophenyl group and a 4-piperidinyloxy group. This combination of aromatic and nitrogen-containing heterocyclic components is of particular interest for its potential biological activity and ability to interact with specific receptors or enzymes in the body.

The discovery of 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine is part of an ongoing effort to design molecules with enhanced bioactivity and specificity. Pyridine derivatives like this one are known to exhibit a wide range of biological activities, such as antimicrobial, anti-inflammatory, and anticancer properties. The introduction of functional groups like the 4-chlorophenyl and 4-piperidinyloxy moieties further expands the chemical diversity of the compound, allowing for potential applications in different therapeutic areas.

One of the primary areas of application for 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine is in the development of compounds that can modulate the central nervous system (CNS). The piperidinyloxy group is a known pharmacophore that can interact with neurotransmitter receptors, such as those involved in the regulation of acetylcholine and dopamine. As a result, compounds like this one have the potential to be developed as neuroactive agents, possibly for the treatment of conditions such as Alzheimer's disease, Parkinson's disease, or schizophrenia. The presence of the 4-chlorophenyl group, which can influence the compound's lipophilicity and binding affinity, may also enhance its ability to cross the blood-brain barrier and reach its target sites within the CNS.

In addition to its neuropharmacological potential, 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine could also find applications in other therapeutic areas. The chlorophenyl group is often associated with antimicrobial and anticancer activity, suggesting that this compound may possess similar properties. Researchers could explore its potential as an antimicrobial agent, particularly in the development of drugs targeting bacterial infections or as an anticancer agent by evaluating its cytotoxic effects on various cancer cell lines. The versatility of the compound makes it an attractive candidate for further investigation and development.

Furthermore, this compound's properties could make it valuable in the design of new drug delivery systems. Its ability to interact with specific receptors may be leveraged to create prodrugs or drug conjugates that release the active drug in a controlled manner, potentially improving the therapeutic index of drugs used for chronic conditions or targeted therapies.

Given the wide range of biological activities associated with pyridine derivatives and the unique combination of functional groups in 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine, this compound holds promise as a lead compound for the development of novel pharmacological agents. Its potential applications span several therapeutic areas, from CNS disorders to cancer and antimicrobial therapies. Continued research into its pharmacological properties and structural modifications will be necessary to fully realize its potential in drug development.

References

2003. Bepotastine besilate. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0062