26163-40-6

Usage

Uses

Used in Research Applications:
(4-Chlorophenyl)(piperidin-1-yl)methanone is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its structural and functional similarities to ketamine make it a valuable tool for investigating the mechanisms of action and potential therapeutic applications of dissociative drugs.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (4-Chlorophenyl)(piperidin-1-yl)methanone may be utilized as a starting point for the development of new medications with improved safety profiles and reduced potential for abuse. Its dissociative and analgesic properties could be harnessed to create novel treatments for pain management and other conditions, provided that the risks associated with its psychoactive effects are mitigated.
Used in Forensic Toxicology:
(4-Chlorophenyl)(piperidin-1-yl)methanone's classification as a controlled substance necessitates its detection and analysis in forensic toxicology. It is used as a reference compound for the identification and quantification of designer drugs in biological samples, such as blood or urine, to support legal proceedings and public health initiatives.

InChI:InChI=1/C12H14ClNO/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 
• 74-11-3 para-chlorobenzoic acid 
• 32792-54-4 2,4-dinitrophenyl 4-chlorobenzoate 
• 3335-29-3 (4-chlorophenyl)(piperidin-1-yl)methanethione 
• 6264-29-5 4-nitrophenyl 4-chlorobenzoate 
• 24252-90-2 S-(p-nitrophenyl) p-chlorothiobenzoate 
• 122-01-0 4-chloro-benzoyl chloride 
• 17459-75-5 3-chlorophenyl 4-chlorobenzoate 
• 73686-49-4 4-Chloro-benzoic acid pyridin-2-yl ester 
• 100-02-7 4-nitro-phenol 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 2156-71-0 N-chloropiperidine 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 143901-82-0 C₂₄H₂₈Cl₂N₂ 
• 143901-81-9 C₂₄H₂₈Cl₂N₂ 
• 3335-29-3 (4-chlorophenyl)(piperidin-1-yl)methanethione 
• 137374-28-8 N-benzyl-4-chloro-N-methylbenzamide 
• 59507-42-5 1-(4-chlorobenzyl)piperidine 
• 59746-58-6 (4-ethylphenyl)(piperidin-1-yl)methanone 
• 42837-37-6 4-(N-piperidinocarbonyl)aniline 
• 411209-38-6 (piperidin-1-yl)-(4-(trifluoromethyl)phenyl)methanone 
• 76335-56-3 1-[(2,3-Dihydro-4H-1,4-benzodioxin)-2-ylmethyl]-4-(4-chloro-benzoyl)piperidine 

Relevant academic research and scientific papers

Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

Catalytic N-Acylation of Cyclic Amines by Arylglyoxylic Acids via Radical-Radical Cross-Coupling

A methodical mechanistic investigation allowed for the catalytic N-acylation of secondary cyclic amine counterparts by arylglyoxylic acids through radical-radical coupling. The reaction proceeds via a twofold SET-promoted Cu(I)/Cu(II) catalytic cycle under mild conditions. An analogous reaction variant allows for the N-acylation in a one-pot fashion directly starting from a secondary cyclic amine even in the presence of a second amine or hydroxy group.

Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions

In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.

Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol

The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.

Amidation of Aldehydes with Amines under Mild Conditions Using Metal-Organic Framework Derived NiO@Ni Mott-Schottky Catalyst

Here we report a facile method for the synthesis of nickel oxide-nickel (NiO@Ni) Mott-Schottky catalyst employing metal-organic framework (MOF) as the precursor. A direct amidation protocol of aldehydes with amines has been optimized under mild conditions using NiO@Ni Mott-Schottky catalyst and it shows far better catalytic activity than the NiO?Ni nanoparticles prepared from simple Ni2+ salt under similar reaction conditions. The heterogeneous catalyst is robust, recyclable and efficient to provide comparable yield to costly ligand-based homogeneous Ni catalysts. The scope of the reaction protocol has been explored with variably substituted substrates. The reaction initiates by homolytic cleavage of peroxide and proceeds through radical mechanism.

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.

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.

Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides

A novel metal-free oxidative-amidation strategy for the synthesis of α-ketothioamides and amides from α-azido ketones was developed. The C-H bond thionation of α-azido ketones with elemental sulfur could form α-ketothioacyl azide, which was then nucleophilically attacked by amines, causing the cleavage of the C-N bond to afford α-ketothioamides, while amides could be formed with the release of nitrogen gas and cyano anion in the presence of PhI(OAc)2 by selective C-C bond cleavage.

Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides

A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.

1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions

Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.