57707-20-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-N-cyclohexylbenzamide is used as a pharmaceutical intermediate for the synthesis of various drugs, contributing to the development of new therapeutic agents.
Used in Central Nervous System Stimulation:
4-Chloro-N-cyclohexylbenzamide is used as a central nervous system stimulant, potentially enhancing cognitive function and alertness.
Used in Anesthetic Applications:
Due to its local anesthetic properties, 4-Chloro-N-cyclohexylbenzamide is used in the development of anesthetics for medical procedures to manage pain.
Used in Pain Management:
4-Chloro-N-cyclohexylbenzamide is used as a pain management agent, potentially providing relief from acute and chronic pain conditions.
Used in Antiviral Drug Development:
4-Chloro-N-cyclohexylbenzamide is used in antiviral research for its potential to inhibit viral replication, with applications in the development of new antiviral drugs to combat viral infections.

InChI:InChI=1/C13H16ClNO/c14-11-8-6-10(7-9-11)13(16)15-12-4-2-1-3-5-12/h6-9,12H,1-5H2,(H,15,16)

Upstream product

• 931-53-3 Cyclohexyl isocyanide 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 201230-82-2 carbon monoxide 
• 108-91-8 cyclohexylamine 
• 52670-38-9 2-ethynylaniline 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 104-86-9 4-chlorobenzylamine 
• 3712-40-1 tert-butyl cyclohexylcarbamate 
• 25070-80-8 prop-2'-en-1'-yl cyclohexylcarbamate 
• 3173-53-3 Cyclohexyl isocyanate 
• 1919-45-5 2,4,6-tris(4-chlorophenoxy)-1,3,5-triazine 
• 99-91-2 para-chloroacetophenone 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Downstream Products

• 99231-40-0 N-cyclohexyl 4-chlorobenzimidoyl chloride 
• 1246564-66-8 C₁₉H₂₀ClN₃O 
• 55501-45-6 2-chloro-N-(4-nitrophenyl)benzamide 

Relevant academic research and scientific papers

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Oxidative Amidation of Amines in Tandem with Transamidation: A Route to Amides Using Visible-Light Energy

A methodology is reported for preparing amides using amines as an acyl source. The protocol involves the visible-light-promoted oxidative amidation of amines with pyrazole to synthesize N-acyl pyrazoles followed by transamidation. By combining photoredox catalysis with oxoammonium cations in the presence of sodium persulfate as a terminal oxidant, the N-acyl pyrazoles could be prepared efficiently and effectively using blue LEDs. The transamidation step was performed without the need to purify the N-acyl pyrazole intermediate, and a range of amides were generated in good to excellent yields.

Nickel-catalyzed reductive amidation of aryl-triazine ethers

The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.

Copper(II)-Photocatalyzed N-H Alkylation with Alkanes

We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.

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.

Integration of co2 reduction with subsequent carbonylation: Towards extending chemical utilization of co2

Currently, it still remains a challenge to amplify the spectrum of chemical fixation of CO2, although enormous progress has been achieved in this field. In view of the widespread applications of CO in a myriad of industrial carbonylation processes, an alternative strategy is proposed in which CO2 reduction to CO is combined with carbonylation with CO generated ex situ, which affords efficiently pharmaceutically and agrochemically attractive molecules. As such, CO2 in this study was efficiently reduced by triphenysilane using CsF to CO in a sealed two-chamber reactor. Subsequently, palladium-catalyzed aminocar-bonylation, carbonylative Sonogashira coupling of aryl iodides, and rhodium(I)-mediated Pauson–Khand-type reaction proceeded smoothly to yield amides, alkynones, and bicyclic cy-clopentenones, respectively. Furthermore, the formed alkynones can further be successfully converted to a series of heterocycles, for example, pyrazoles, 3a-hydroxyisoxazolo[3,2-a]isoindol-8-(3aH)-one derivatives and pyrimidines in moderate yields. The striking features of this protocol include operational simplicity, high efficiency, and relatively broad application scope, which represents an alternative avenue for CO2 transformation.

A high-efficient method for the amidation of carboxylic acids promoted by triphenylphosphine oxide and oxalyl chloride

A effective amidation reaction of carboxylic acids with various amines promoted by triphenylphosphine oxide and oxalyl chloride under mild and neutral conditions has been developed. The feature of this procedure was the using and recycling of triphenylphosphine oxide at room temperature in 0.5?h. Furthermore a plausible mechanism also be deduced with the help of 31P NMR spectroscopy.

Atom economical synthesis of: N -alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant

A green and mild synthetic route to N-alkylbenzamides involves eco-friendly one pot synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(iii) sulfate catalyzed rearrangement to the corresponding amides in water as the solvent and in the presence of sodium dodecyl sulfate as the surfactant. This green approach affords N-alkylbenzamides in high overall yields under simple and minimum manipulation.

The copper-catalyzed cross-coupling reactions of aryl diazonium salts and isocyanides

The copper-catalyzed cross-coupling reaction of aryl diazonium salts and isocyanides has been performed. This is a successful example of preparation of arylcarboxyamides with moderate to good yield under mild conditions.

Nickel-Catalyzed Reductive Addition of Aryl/Benzyl Halides and Pseudohalides to Carbodiimides for the Synthesis of Amides

A Nickel-catalyzed reductive process is described for the direct amidation of benzyl and aryl halides using carbodiimides as the amidating agent. Moreover, aryl and benzyl C–O electrophiles such as triflate, acetate, tosylate, trityl ether, and pivalate were converted into amides using this method. The in-situ-generated Ni0acts as a catalyst for the reaction at room temperature for benzylic substrates, and 70 °C for aryl electrophiles. This new nickel-catalyzed reductive coupling protocol provides a general and operationally simple method for the synthesis of diverse amides using carbodiimides. Amides bearing bulky substituents can be synthesized by this strategy in high yield, which demonstrates its effectiveness in amide synthesis.