1-(2-Pyridyl)piperazine

Base Information

• Chemical Name: 1-(2-Pyridyl)piperazine
• CAS No.: 34803-66-2
• Molecular Formula: C9H13N3
• Molecular Weight: 163.222
• Hs Code.: 29339900
• European Community (EC) Number: 252-220-3
• NSC Number: 137781
• UNII: 5IO1HZP7ZN
• DSSTox Substance ID: DTXSID90188341
• Nikkaji Number: J208.913K
• Wikipedia: Pyridinylpiperazine
• Wikidata: Q7263585
• ChEMBL ID: CHEMBL18094
• Mol file: 34803-66-2.mol

Synonyms:1-(2-pyridinyl)piperazine;1-(2-pyridinyl)piperazine, sodium salt

Chemical Property of 1-(2-Pyridyl)piperazine

Chemical Property:

• Appearance/Colour: clear colourless to yellow liquid
• Vapor Pressure: 0.000467mmHg at 25°C
• Melting Point: 92-94 °C
• Refractive Index: n20/D 1.595(lit.)
• Boiling Point: 314.4 °C at 760 mmHg
• PKA: 8.63±0.10(Predicted)
• Flash Point: 143.9 °C
• PSA: 28.16000
• Density: 1.081 g/cm³
• LogP: 0.88500
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: Soluble in Chloroform, Methanol.
• Water Solubility.: >500 g/L (20 ºC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 163.110947427
• Heavy Atom Count: 12
• Complexity: 132

Purity/Quality:

98% ^*data from raw suppliers

1-(Pyridin-2-yl)piperazine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCN1)C2=CC=CC=N2
• General Description: 1-(2-Pyridyl)piperazine is a pyridinylpiperazine derivative identified as a selective α₂-adrenoceptor antagonist, with its 3-fluoro-substituted variant (2b) demonstrating particularly high potency and selectivity compared to established reference compounds like yohimbine. 1-(2-Pyridyl)piperazine class shows promise for therapeutic applications targeting α₂-adrenoceptor-mediated pathways.

Technology Process of 1-(2-Pyridyl)piperazine

There total 9 articles about 1-(2-Pyridyl)piperazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

tert-butyl 4-(pyridin-2-yl)piperazine-1-carboxylate (77278-62-7) → 1-(2-pyridyl)piperazine (34803-66-2)

Guidance literature:

tert-butyl 4-(pyridin-2-yl)piperazine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 30 ℃; for 1h;

With sodium hydroxide; In dichloromethane; water; pH=9;

Reference yield: 94.0%

piperazine (110-85-0) + 2-chloropyridine (109-09-1) → 1-(2-pyridyl)piperazine (34803-66-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 0.166667h; Temperature;

DOI:10.1021/acs.orglett.6b02591

Reference yield: 94.0%

ethyl-4-(2-pyridyl)-1-piperazine carboxylate (158399-58-7) → 1-(2-pyridyl)piperazine (34803-66-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0040-4020(99)00788-7

upstream raw materials:

piperazine

2-bromo-pyridine

ethyl-4-(2-pyridyl)-1-piperazine carboxylate

2-chloropyridine

Downstream raw materials:

2-<4-(pyridin-2-yl)piperazin-1-yl>ethanol

1,1-diphenyl-2-(4-pyridin-2-yl-piperazin-1-yl)-ethanol

1-[2-(N-ethyl-anilino)-ethyl]-4-[2]pyridyl-piperazine

1-methyl-4-(pyridin-2-yl)piperazine

Refernces

Pyridinylpiperazines, a new class of selective α₂-adrenoceptor antagonists

10.1021/jm00366a007

The research aimed to synthesize and evaluate a series of 1-(2-pyridinyl)piperazine derivatives for their adrenergic activity, specifically as selective a2-adrenoceptor antagonists. The study used various 2-halo-pyridines and piperazines to synthesize the target compounds. Key chemicals included 2-chloro-3-fluoropyridine, piperazine, N-methylpiperazine, and several other halogenated pyridines. The researchers assessed the in vitro activity of these compounds by measuring their ability to displace [3H]clonidine and [3H]prazosin from membrane binding sites in calf cerebral cortex, which indicated their interaction with a2- and a1-adrenoceptors, respectively. In vivo assays involved antagonism of clonidine-induced mydriasis in rats. The study concluded that several compounds, particularly the 3-fluoro derivative (2b), exhibited higher potency and selectivity for a2-adrenoceptors compared to reference standards like yohimbine and rauwolscine. The research suggests that these pyridinylpiperazines could serve as potential therapeutic agents for conditions involving a2-adrenoceptor modulation.