1-(2-Pyridyl)piperazine
[CAS# 34803-66-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: 1-(2-Pyridyl)piperazine
• Synonyms: 1-(2-Pyridinyl)piperazine
• Molecular Formula: C₉H₁₃N₃
• Molecular Weight: 163.22
• CAS Registry Number: 34803-66-2
• EC Number: 252-220-3
• SMILES: C1CN(CCN1)C2=CC=CC=N2

Properties

• Density: 1.072
• Boiling point: 293 ºC
• Refractive index: 1.593-1.595
• Water solubility: >500 g/L (20 ºC)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H314-H315-H319-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

1-(2-pyridyl)piperazine, commonly abbreviated as 2-PP, is a compound with applications in medicinal chemistry and organic synthesis. The discovery of 1-(2-pyridyl)piperazine can be traced back to mid-20th century efforts to explore the potential of piperazine derivatives in medicinal chemistry. Piperazine is a heterocyclic compound with a six-membered ring containing two nitrogen atoms, known for its versatility and pharmacological activity. Attaching a pyridine ring to piperazine results in new compounds with unique chemical properties and biological activities.

The structure of 1-(2-pyridyl)piperazine consists of a piperazine ring and a 2-pyridine ring. This arrangement allows for multiple interactions with biological targets, as both ring nitrogen atoms can participate in hydrogen bonding and coordination with metal ions, thus affecting the reactivity and biological activity of the compound.

1-(2-pyridyl)piperazine has attracted attention primarily for its role in medicinal chemistry, as a key intermediate in the synthesis of various therapeutic agents. Its structure provides a versatile scaffold for the design of drugs targeting a range of receptors and enzymes. One prominent application is the development of psychoactive drugs, especially those acting on the central nervous system (CNS).

In the field of psychiatry, 1-(2-pyridyl)piperazine derivatives are used to develop drugs that modulate neurotransmitter systems. These derivatives interact with serotonin receptors, which play a crucial role in mood regulation, anxiety, and depression. For example, some antidepressants and antipsychotics utilize the 2-PP structure to enhance their efficacy by affecting the serotonin pathway.

The compound's ability to act as a pharmacophore, the part of the molecule responsible for its biological activity, makes it valuable in designing drugs with specific binding affinity and selectivity characteristics, improving the efficacy of drugs for the treatment of psychiatric disorders and reducing side effects.

In addition to psychiatric applications, 1-(2-pyridyl)piperazine is also used in the development of cardiovascular drugs, especially antihypertensive drugs. Its derivatives can act on various receptors involved in blood pressure regulation, such as the α-adrenergic receptor, contributing to its effective control of hypertension. The compound's structure allows for modification of binding properties to create drugs that target specific cardiovascular pathways.

In organic synthesis, 1-(2-pyridyl)piperazine is valued for its role as a building block for constructing complex molecules. Its structure facilitates a variety of chemical reactions, including nucleophilic substitution and coupling reactions, making it a useful intermediate for the synthesis of heterocyclic compounds. This versatility is essential for developing new synthetic methods and expanding the toolkit of chemists for creating a variety of chemical entities.

The compound's ability to form metal complexes as a ligand also highlights its importance in catalytic reactions. These complexes can be used in homogeneous catalysis, improving reaction rates and selectivity in industrial processes and academic research.

Ongoing research focuses on exploring its potential for drug discovery and synthetic applications. Research aims to optimize its synthesis, improve the pharmacological properties of its derivatives, and understand its interactions with biological targets. These efforts help advance new therapeutic agents and develop innovative synthetic methods.