5-[(4-Ethyl-1-piperazinyl)methyl]-2-pyridinamine
[CAS# 1180132-17-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Ethylpyridine
• Name: 5-[(4-Ethyl-1-piperazinyl)methyl]-2-pyridinamine
• Synonyms: [5-[(4-Ethylpiperazin-1-yl)methyl]pyridin-2-yl]amine
• Molecular Formula: C₁₂H₂₀N₄
• Molecular Weight: 220.31
• CAS Registry Number: 1180132-17-5
• EC Number: 806-688-6
• SMILES: CCN1CCN(CC1)CC2=CN=C(C=C2)N

Properties

• Density: 1.1$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 362.4$+/-$37.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 173.0$+/-$26.5 $degree$C (Calc.)^*
• Index of refraction: 1.578 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

5-[(4-Ethyl-1-piperazinyl)methyl]-2-pyridinamine is an organic compound belonging to the class of substituted piperazine derivatives linked to an aminopyridine moiety. Compounds of this type have been investigated extensively in medicinal chemistry due to their pharmacological potential, particularly in modulating central nervous system targets, receptor binding, and enzyme inhibition. Piperazine derivatives, known since the late nineteenth century, became important scaffolds in pharmaceutical research during the mid-to-late twentieth century, when systematic studies explored the effects of N-substitution and heteroaryl attachments on biological activity. The structure of 5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinamine contains a pyridine ring substituted at the 2-position with an amino group and at the 5-position with a methylene-linked N-ethylpiperazine. The piperazine ring provides a flexible tertiary nitrogen site capable of participating in hydrogen bonding or ionic interactions, while the ethyl substitution influences steric and electronic properties, affecting solubility and receptor interactions. The amino group on the pyridine ring adds basicity and hydrogen bonding potential, which is significant in the compound’s interaction with biological targets. Synthetically, compounds of this type are generally prepared through nucleophilic substitution reactions. A halomethyl-pyridine precursor reacts with 4-ethylpiperazine under controlled conditions to form the methylene-linked piperazine derivative. The reaction is followed by purification and characterization steps to ensure the correct structural configuration. The combination of the pyridine ring and the piperazine scaffold is a common strategy in drug design, providing both aromaticity for π-stacking interactions and a flexible nitrogen-containing moiety for receptor binding. The primary applications of 5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinamine are in medicinal chemistry and pharmaceutical research. Substituted piperazines connected to aminopyridines have been used as intermediates in the synthesis of drugs targeting neurotransmitter receptors, such as serotonin and dopamine receptors, and in the development of kinase inhibitors. The structural features of this compound allow it to function as a scaffold that can be further modified to enhance selectivity, potency, and pharmacokinetic properties. The compound’s pharmacological relevance also stems from the combination of aromatic and basic nitrogen functionalities, which permits interaction with a variety of biological targets. The pyridine nitrogen and amino group can form hydrogen bonds and coordinate with metal ions in enzyme active sites, while the piperazine moiety provides conformational flexibility that facilitates optimal binding. This dual functionality has made such compounds valuable in structure-activity relationship studies for optimizing drug candidates. In addition to biological applications, 5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinamine serves as a versatile intermediate in synthetic organic chemistry. The amino group and piperazine nitrogen are available for further derivatization, including acylation, alkylation, and formation of salts or prodrugs. These transformations allow chemists to design a wide range of derivatives with tailored properties for both chemical and pharmacological applications. Overall, 5-[(4-ethyl-1-piperazinyl)methyl]-2-pyridinamine exemplifies the utility of N-substituted piperazine-aminopyridine derivatives in medicinal chemistry. Its combination of a pyridine ring, an amino group, and a substituted piperazine moiety provides a flexible and functional scaffold for the design of biologically active molecules. The compound has contributed to research in synthetic methodology, drug design, and the understanding of molecular interactions important in pharmaceutical science.

References

2018. Abemaciclib. Pharmaceutical Substances.