58547-67-4

Usage

Uses

Used in Pharmaceutical Research and Development:
N-(4-Fluorobenzoyl)piperidine is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of drugs that target specific biological receptors or enzymes. This application is crucial for the development of new therapeutic agents with precise mechanisms of action.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-(4-fluorobenzoyl)piperidine is utilized as a building block for the creation of novel drug candidates. Its unique structure allows for the design of molecules with potential therapeutic effects, contributing to the advancement of treatments for various diseases and conditions.
Used in Industrial Applications:
Beyond its pharmaceutical applications, N-(4-fluorobenzoyl)piperidine may also serve as a component in the production of polymers and other materials. Its versatility in chemical reactions and potential to enhance material properties makes it a candidate for use in various industrial processes.

InChI:InChI=1/C12H14FNO/c13-11-6-4-10(5-7-11)12(15)14-8-2-1-3-9-14/h4-7H,1-3,8-9H2

Upstream product

• 110-89-4 piperidine 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 2156-71-0 N-chloropiperidine 
• 459-56-3 4-fluorobenzylic alcohol 
• 403-43-0 4-fluorobenzoyl chloride 
• 201230-82-2 carbon monoxide 
• 332-01-4 1-((4-fluorophenyl)diazenyl)piperidine 
• 371-40-4 4-fluoroaniline 
• 139592-92-0 4-fluorobenzylpiperidine 
• 1765-93-1 4-fluoroboronic acid 
• 1013-92-9 di(piperidin-1-yl)methanethione 
• 352-32-9 p-fluorotoluene 
• 579-39-5 1,2-bis(4-fluorophenyl)ethane-1,2-dione 

Downstream Products

• 139592-92-0 4-fluorobenzylpiperidine 

Relevant academic research and scientific papers

Synthesis and studies on gem-fluorinated 2-azabicyclo[n.1.0]alkanes

Three novel amines all possessing gem-difluorocyclopropane, secondary amino group and a fused aliphatic cycle were synthesized by difluorocyclopropanation of N-Boc protected enamides. The compounds were stable when amino group was blocked by protonation o

Palladium-Catalyzed Desulfurative Amide Formation from Thioureas and Arylboronic Acids

The development of the reactivity on carbene complexes would lead to the creation of novel synthetic strategies. We discovered herein the Pd-catalyzed desulfurative amide formation involved Suzuki-Miyaura coupling reaction, notably the Pd complex was generated in situ from thioureas, Ag salt and Pd catalyst. Silver salt was essential for the construction of this type of carbenes from available and stable thioureas and well participated in the catalytic cycle. We report a method for the synthesis of arylamides from arylboronic acids, which greatly enriched the application of thiourea chemistry and expanded the application of the Suzuki-Miyaura coupling.

Electrochemical Amide Bond Formation from Benzaldehydes and Amines: Oxidation by Cathodic-Generated Hydrogen Peroxide

Although amide bond formation from aldehydes and amines is a popular synthetic tool, most of the previously reported reactions depend on transition-metal catalysts or expensive oxidants. We considered that a more environmentally benign and safer approach could be achieved by electrochemistry. Nineteen benzamide derivatives were obtained with this reaction. NMR studies, cyclic voltammetry (CV) investigations, and control experiments showed that the corresponding intermediate, a hemiaminal, was transformed into the amide by oxidation with hydrogen peroxide generated in situ by cathodic reduction of molecular oxygen.

Cobalt-catalyzed aminocarbonylation of (hetero)aryl halides promoted by visible light

The catalytic aminocarbonylation of (hetero)aryl halides is widely applied in the synthesis of amides but relies heavily on the use of precious metal catalysis. Herein, we report an aminocarbonylation of (hetero)aryl halides using a simple cobalt catalyst under visible light irradiation. The reaction extends to the use of (hetero)aryl chlorides and is successful with a broad range of amine nucleophiles. Mechanistic investigations are consistent with a reaction proceeding via intermolecular charge transfer involving a donor-acceptor complex of the substrate and cobaltate catalyst.

Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas

A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.

Visible-Light-Mediated Efficient Metal-Free Catalyst for α-Oxygenation of Tertiary Amines to Amides

A metal-free system has been discovered for the efficient α-oxygenation of tertiary amines to the corresponding amides using oxygen as an oxidant. This visible-light-mediated oxygenation reaction exhibited excellent substrates scope under mild reaction conditions and generated water as the only byproduct. The synthetic utility of this approach has been demonstrated by applying onto drug molecules. At the end, detailed mechanistic reactions clearly showed the role of oxygen and the photocatalyst.

Copper-Catalyzed Carbonylative Cross-Coupling of Arylboronic Acids with N-Chloroamines for the Synthesis of Aryl Amides

A novel copper-catalyzed carbonylative cross-coupling between N-chloroamines and arylboronics acids has been developed. With copper(I) oxide as the catalyst, various desired amide compounds were produced in moderate to good yields. Functional groups such as iodide and alkene are tolerated. Notably, this is the first example of a copper-catalyzed aminocarbonylation with N-chloroamines.

Palladium-Catalyzed Carbonylative Synthesis of Amides from Aryltriazenes under Additive-Free Conditions

An interesting palladium-catalyzed carbonylative synthesis of amides from aryltriazenes was developed. By using Pd(MeCN2)Cl2 as the catalyst precursor under CO pressure through a N2 extrusion/CO insertion sequence, a broad range of aryltriazenes were transformed into the corresponding amides in good yields with excellent functional group tolerance. Remarkably, no additives such as acids or phosphine ligands were required.

Copper-Catalyzed Aerobic Oxidative Amidation of Benzyl Alcohols

A Cu-catalyzed synthesis of amides from alcohols and secondary amines using the oxygen in air as the terminal oxidant has been developed. The methodology is operationally simple requiring no high pressure equipment or handling of pure oxygen. The commercially available, nonprecious metal catalyst, Cu(phen)Cl2, in conjunction with di-tert-butyl hydrazine dicarboxylate and an inorganic base provides a variety of benzamides in moderate to excellent yields. The pKa of amine conjugate acid and electronics of alcohol were shown to impact the selection of base for optimal reactivity. A mechanism consistent with the observed reactivity trends, KIE, and Hammett study is proposed.

Iron-catalyzed direct synthesis of amides from methylarenes

An efficient, green and first catalytic process has been developed for the direct synthesis of amides from readily available petroleum by-products (methylarenes) and amines using an iron catalyst. In this new catalytic reaction, the methyl group of the me