2767-90-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1-Pyridin-4-ylpiperidine is used as a key intermediate for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its unique structure allows for the creation of diverse chemical entities with potential therapeutic or pesticidal properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1-Pyridin-4-ylpiperidine is employed as a valuable research compound. It aids in the investigation of novel chemical structures and their interactions with biological targets, which is crucial for the discovery of new therapeutic agents.
Used in Coordination Chemistry as a Ligand:
1-Pyridin-4-ylpiperidine is utilized as a ligand in coordination chemistry, where it forms complexes with metal ions. These complexes have potential applications in various areas, such as catalysis, materials science, and the development of new functional materials.
Used in Organic Synthesis as a Building Block:
As a building block in organic synthesis, 1-Pyridin-4-ylpiperidine is used to construct more complex organic molecules. Its presence in these molecules can impart specific properties or functions, making it a versatile component in the synthesis of a wide range of organic compounds.

InChI:InChI=1/C10H14N2/c1-2-8-12(9-3-1)10-4-6-11-7-5-10/h4-7H,1-3,8-9H2

Upstream product

• 4783-86-2 4-phenoxypyridine 
• 6091-44-7 piperidine hydrochloride 
• 500356-88-7 4-(piperidin-1-yl)picolinic acid 
• 110-89-4 piperidine 
• 626-61-9 4-Chloropyridine 
• 626-55-1 3-Bromopyridine 
• 110-86-1 pyridine 
• 707-74-4 (trichloromethyl)mesitylene 
• 100-48-1 pyridine-4-carbonitrile 
• 5470-22-4 4-chloropicolinic acid 
• 2156-71-0 N-chloropiperidine 
• 19524-06-2 4-bromopyridine hydrochloride 
• 620-08-6 4-methoxypyridine 
• 15854-87-2 4-iodopyridine 

Downstream Products

• 120357-02-0 1-[2-(2-ethoxycarbonylaminobenzenesulfonyl)aminoethyl]-4-(4-fluorobenzoyl)piperidine 
• 1294499-14-1 1-[4-(bromomethyl)benzyl]-4-piperidin-1-ylpyridinium bromide 

Relevant academic research and scientific papers

LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase

Eleven derivatives of 1,1′-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electron-releasing, neutral or electron-withdrawing groups. A one-parameter regression equation has been derived which satisfactorily describes the ex vivo inhibitory potency of ChoK of the title compounds. The electronic effect plays a critical function in the ex vivo inhibition of ChoK although the role of electrostatic interactions could be altered due to a solvation process of both ChoK and ligands.

Microwave-promoted piperidination of halopyridines: A comparison between Ullmann, Buchwald-Hartwig and uncatalysed SNAr reactions

A comparative study between the most used methodologies for the preparation of piperidinyl pyridines (Buchwald-Hartwig reaction, Ullmann reaction and nucleophilic aromatic substitution (SNAr)) by microwave-assisted piperidination of halopyridines is reported. Our results suggest that the Ullmann reaction is most effective for less reactive halopyridines, while uncatalysed SNAr is sufficient for more reactive ones. Copyright

Cu(II)-catalyzed C-N coupling of (hetero)aryl halides and N-Nucleophiles promoted by α-benzoin oxime

We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaαolds found in FDA-approved pharmaceuticals.

Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades

Herein, we report a strategy for the generation of nitrogen-radicals by ground-state single electron transfer with organyl–NiI species. Depending on the philicity of the N-radical, two types of processes have been developed. In the case of nucleophilic aminyl radicals direct N-arylation with aryl organozinc, organoboron, and organosilicon reagents was achieved. In the case of electrophilic amidyl radicals, cascade processes involving intramolecular cyclization, followed by reaction with both aryl and alkyl organometallics have been developed. The N-cyclization–alkylation cascade introduces a novel retrosynthetic disconnection for the assembly of substituted lactams and pyrrolidines with its potential demonstrated in the short total synthesis of four venom alkaloids.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Nucleophilic amination of methoxypyridines by a sodium hydride-iodide composite

A new protocol for nucleophilic amination of methoxypyridines and their derivatives was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The method offers a concise access to various aminopyridines which are potentially of medicinal interest.

An Improved Rapid and Mild Deoxygenation of Amine N-oxides

An improved mild and selective method for the deoxygenation of a variety of amine N-oxides has been carried out in the presence of silica gel under mild conditions at room temperature to afford corresponding amines in relatively good yields without purification. The reaction is tolerant of a variety of functional groups such as hydroxyl, ester, acid, carbonyl, and cyano groups, as well as halogens. This method would be of great utility to synthesize various pyridines and amines easily.

Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition

A clean, mild and sustainable method for the functionalization of pyridines and their analogues is reported. A zinc-based Lewis acid is used to activate pyridine and its analogues towards nucleophilic aromatic substitution, conjugate addition, and cyclization reactions by binding to the nitrogen on the pyridine ring and activating the pyridine ring core towards further functionalization.

Homodimeric bis-quaternary heterocyclic ammonium salts as potent acetyl- and butyrylcholinesterase inhibitors: A systematic investigation of the influence of linker and cationic heads over affinity and selectivity

A molecular library of quaternary ammonium salts (QASs), mainly composed of symmetrical bis-quaternary heterocyclic bromides exhibiting choline kinase (ChoK) inhibitory activity, were evaluated for their ability to inhibit acetyl- and butyrylcholinesterase (AChE and BChE, respectively). The molecular framework of QASs consisted of two positively charged heteroaromatic (pyridinium or quinolinium) or sterically hindered aliphatic (quinuclidinium) nitrogen rings kept at an appropriate distance by lipophilic rigid or semirigid linkers. Many homodimeric QASs showed AChE and BChE inhibitory potency in the nanomolar range along with a low enzymatic selectivity. Computational studies on AChE, BChE, and ChoK allowed identification of the key molecular determinants for high affinity and selectivity over either one of the three enzymes and guided the design of a hybrid bis-QAS (56) exhibiting the highest AChE affinity (IC50 = 15 nM) and selectivity over BChE and ChoK (SI = 50 and 562, respectively) and a promising pharmacological potential in myasthenia gravis and neuromuscular blockade.

Transition-metal-free electrophilic amination between aryl grignard reagents and N-chloroamines

In the presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) as an additive, easily prepared and handled N-chloroamines react with aryl Grignard reagents to give a variety of arylamines in good to excellent yields. Functional groups such as ester and nitrile are compatible under the reaction conditions (Figure Presented).