145208-85-1

Basic information

• Product Name: Piperazine, 1-methyl-4-(2-pyridinyl)- (9CI)
• Synonyms: Piperazine, 1-methyl-4-(2-pyridinyl)- (9CI);1-METHYL-4-PYRIDIN-2-YLPIPERAZINE;1-Methyl-4-(2-pyridinyl)-piperazine;Piperazine, 1-Methyl-4-(2-pyridinyl)-
• CAS NO: 145208-85-1
• Molecular Formula: C₁₀H₁₅N₃
• Molecular Weight: 177.2462
• Product Categories: PIPERIDINE;pharmacetical
• Mol File: 145208-85-1.mol

Chemical Properties

• Boiling Point: 290.2°Cat760mmHg
• Flash Point: 129.3°C
• Appearance: /
• Density: 1.067g/cm³
• Vapor Pressure: 0.0021mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: Piperazine, 1-methyl-4-(2-pyridinyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 1-methyl-4-(2-pyridinyl)- (9CI)(145208-85-1)
• EPA Substance Registry System: Piperazine, 1-methyl-4-(2-pyridinyl)- (9CI)(145208-85-1)

Safety Data

• Hazardous Substances Data: 145208-85-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H15N3/c1-12-6-8-13(9-7-12)10-4-2-3-5-11-10/h2-5H,6-9H2,1H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 109-04-6 2-bromo-pyridine 
• 1628-89-3 2-methoxypyridine 
• 109-09-1 2-chloropyridine 
• 100-70-9 2-Cyanopyridine 
• 504-29-0 2-aminopyridine 
• 105-59-9 N-Methyldiethanolamine 
• 15103-48-7 pyridine-2-sulfonic acid 
• 874493-33-1 pyridin-2-yl N,N,N',N'-tetramethyldiamidophosphate 
• 142-08-5 2-hydroxypyridin 
• 50-00-0 formaldehyd 
• 34803-66-2 1-(2-pyridyl)piperazine 

Relevant articles and documents

Amination of 2-Pyridinesulfonic and 8-Quinolinesulfonic Acids with Magnesium Amides

The amination of 2-pyridine- and 8-quinolinesulfonic acids using magnesium amides of the type R2NMgCl·LiCl is reported. Thus, several cyclic and acyclic amines were converted into the corresponding amides using iPrMgCl·LiCl, which reacted readily with sulfonic acids to produce aminopyridines and aminoquinolines. Various amines which are attractive in drug chemistry were suitable for this transformation.

Buchwald-Hartwig amination of aryl esters and chlorides catalyzed by the dianisole-decorated Pd-NHC complex

A modular and generic method for the Buchwald-Hartwig amination reactions of relatively unreactive aryl esters as acyl electrophiles and aryl chlorides as aryl electrophiles has been developed, leading to the efficient synthesis of amides/amines under air conditions and with low catalyst loadings. The success of this catalytic protocol is mainly attributed to the modification of the Pd-IPr skeleton with sterically hindered and electron-donating anisole groups. This method also features good functional group tolerance and excellent chemoselectivities. In summary, the results presented herein suggest the possibility of developing a versatile and general protocol for diverse electrophiles to undergo the Buchwald-Hartwig amination reactions, avoiding too much consideration of the reaction conditions for the substrate-dependent C-N bond formations.

Iridium/graphene nanostructured catalyst for the: N -alkylation of amines to synthesize nitrogen-containing derivatives and heterocyclic compounds in a green process

A facile iridium/graphene-catalyzed methodology providing an efficient synthetic route for C-N bond formation is reported. This catalyst can directly promote the formation of C-N bonds, without pre-activation steps, and without solvents, alkalis and other additives. This protocol provides a direct N-alkylation of amines using a variety of primary and secondary alcohols with good selectivity and excellent yields. Charmingly, the use of diols resulted in intermolecular cyclization of amines, and such products are privileged structures in biologically active compounds. Two examples illustrate the advantages of this catalyst in organic synthesis: the tandem catalysis to synthesize hydroxyzine, and the intermolecular cyclization to synthesize cyclizine. Water is the only by-product, which makes this catalytic process sustainable and environmentally friendly. This journal is

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

Amination of Phosphorodiamidate-Substituted Pyridines and Related N-Heterocycles with Magnesium Amides

The amination of various phosphorodiamidate-substituted pyridines, quinolines, and quinoxaline with magnesium amides R2NMgCl·LiCl proceeds at room temperature within 8 h. Several pharmaceutically active amines were suitable substrates for this amination procedure, and also the antihistaminic tripelennamine was prepared. Additionally, several heterocyclic phosphorodiamidates underwent directed ortho-metalation (DoM) using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) or TMP2Mg·2LiCl, followed by electrophilic functionalization prior to the amination step, which led to ortho-functionalized aminated N-heterocycles.

Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis

Seven new air- and moisture-stable nickel complexes bearing flexible bulky NHC (N-heterocyclic carbene) ancillary ligands (NHC = IPr, IPrTol, IPrOMe, IPent) are reported. Using experimentally determined crystal structures, the steric

Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride

While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included.

A highly efficient precatalyst for amination of aryl chlorides: Synthesis, structure and application of a robust acenaphthoimidazolylidene palladium complex

A robust palladium NHC complex was synthesized and exhibits exceptional activity and selectivity as a precatalyst in the amination of aryl chlorides and tolerates a wide range of substrates at low catalyst loadings.

Examination of the aromatic amination catalyzed by palladium on charcoal

The Buchwald-Hartwig amination of aryl halides with secondary amines and functionalized aromatic amines catalyzed by solid-supported palladium is reported. The choices of ligand, base and solvent are crucial for the successful coupling. The ami-nation of aromatic iodides, bromides and chlorides can be easily achieved with palladium on charcoal in the presence of a biphenylphosphane-type ligand at 80-110 °C. In addition, the palladium on charcoal catalyst is easily separable after the reaction, and reusable several times with only small activity loss.

Cobalt-catalyzed C-N bond-forming reaction between N-aromatic 2-chlorides and secondary amines

Secondary amines react with N-aromatic 2-chlorides in the presence of a catalytic amount of cobalt chloride. When DPPP was added as ligand, the yield was further improved, The N-aromatic-containing tertiary amines formed are interesting due to their poten