6830-84-8

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxamide, N-methylis used as a solvent in the pharmaceutical industry for the synthesis of various drugs and active pharmaceutical ingredients. Its ability to dissolve a wide range of compounds makes it a versatile solvent in drug manufacturing processes.
Used in Agrochemical Industry:
In the agrochemical industry, Cyclohexanecarboxamide, N-methylserves as a solvent for the production of pesticides, herbicides, and other crop protection agents. Its solubility properties allow for the efficient formulation of these chemicals, ensuring effective delivery to target pests and weeds.
Used in Plastics Industry:
Cyclohexanecarboxamide, N-methylis utilized as a solvent in the plastics industry for the manufacturing of various types of polymers and resins. Its compatibility with a range of monomers and polymers contributes to the production of high-quality plastic materials with desired properties.
Used as an Intermediate in Chemical Production:
Cyclohexanecarboxamide, N-methylis also used as an intermediate in the synthesis of other chemicals, including specialty amines, amides, and other organic compounds. Its reactivity and functional groups make it a valuable building block in organic chemistry.
Overall, Cyclohexanecarboxamide, N-methylis a versatile chemical compound with applications across multiple industries, primarily due to its solubility properties and low toxicity. Its use as a solvent and intermediate in various chemical processes highlights its importance in modern industrial chemistry.

Upstream product

• 74-89-5 methylamine 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 84738-96-5 C₂H₇AlClN 
• 85462-16-4 N-Methyl-O-p-nitrophenylsulphonylhydroxylamine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 52316-19-5 cyclohexyl methyl ketone oxime 
• 593-51-1 methylamine hydrochloride 
• 823-76-7 Cyclohexyl methyl ketone 
• 88070-48-8 N-methylbenzamide 
• 75920-71-7 (1,1-Bis-methylsulfanyl-ethyl)-cyclohexane 
• 80783-98-8 N-methoxy-N-methylcyclohexanecarboxamide 
• 123-39-7 N-Methylformamide 
• 110-83-8 cyclohexene 

Downstream Products

• 100812-16-6 N-(2,2-dimethylpropanoyl)-N-cyclohexanoylmethanamine 
• 25756-29-0 N-methylcyclohexylmethylamine 
• 52316-19-5 cyclohexyl methyl ketone oxime 
• 98-89-5 Cyclohexanecarboxylic acid 
• 100-49-2 cyclohexylmethyl alcohol 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 68571-10-8 cyclohexyl(pyrrolidin-1-yl)methanone 
• 7469-80-9 cyclohexyl 4-methoxyphenyl ketone 
• 2043-61-0 cyclohexanecarbaldehyde 
• 6553-81-7 butyl cyclohexanecarboxylate 
• 1192477-32-9 N-(cyclohexylmethyl)-2-(6-methoxy-1H-indol-3-yl)-N-methyl-2-oxoacetamide 
• 1192477-25-0 N-(cyclohexylmethyl)-2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide 
• 46002-63-5 1-Methyl-5-cyclohexyl-tetrazol 

Relevant academic research and scientific papers

Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.

Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides

First introduced into medicines in the 1930s, the sulfonamide functional group continues to be present in a wide range of contemporary pharmaceuticals and agrochemicals. Despite their popularity in the design of modern bioactive molecules, the underpinning methods for sulfonamide synthesis are essentially unchanged since their introduction, and rely on the use of starting materials with preinstalled sulfur-functionality. Herein we report a direct single-step synthesis of sulfonamides that combines two of the largest monomer sets available in discovery chemistry, (hetero)aryl boronic acids and amines, along with sulfur dioxide, using a Cu(II) catalyst, to deliver a broad range of sulfonamides. Sulfur dioxide is provided by the surrogate reagent DABSO. The reaction tolerates broad variation in both coupling partners, including aryl, heteroaryl and alkenyl boronic acids, as well as cyclic and acyclic alkyl secondary amines, and primary anilines. We validate the method by showing that a variety of drugs, and drug-fragments, can be incorporated into the process.

Efficient one-stage procedure of Beckmann ketones rearrangement in the presence of hydroxylamine

Ketoximes formed from ketones in the presence of hydroxylamine and silica gel in formic acid undergo in situ the Beckmann rearrangement under mild conditions affording in high yields the corresponding amides. Unsymmetrical aromatic ketones, methyl aryl ketones, and methyl cyclohexyl ketone under these conditions form as a rule amides mixtures.

Hydrogen Self-Sufficient Arene Reduction to Cyclohexane Derivatives Using a Combination of Platinum on Carbon and 2-Propanol

Various arenes have been hydrogenated using platinum on carbon in a 2-propanol-aqueous mixed solvent at 100 C without the addition of flammable hydrogen gas to give the corresponding cyclohexane derivatives. 2-Propanol plays a role as an efficient hydrogen source based on the platinum on carbon-catalyzed dehydrogenation.

Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes

Air-stable Rh complexes ligated by strongly σ-donating cyclic (amino)(alkyl)carbenes (CAACs) show unique catalytic activity for the selective hydrogenation of aromatic ketones and phenols by reducing the aryl groups. The use of CAAC ligands is essential for achieving high selectivity and conversion. This method is characterized by its good compatibility with unsaturated ketones, esters, carboxylic acids, amides, and amino acids and is scalable without detriment to its efficiency.

Acid hydrolysis of amides obtained by Beckmann rearrangement of methyl ketones oximes of unsaturated γ-lactone, aromatic, and alicyclic series

Beckmann rearrangement was performed of oximes of substituted 3-acetyl-4-methyl-5,5-dimethyl(pentamethylene)-2-oxo-2,5-dihydrofuranes in the presence of boron trifluoride etherate. Aiming at establishing the spatial arrangement of the oximes the hydrolysis was carried out of acid amides obtained by Beckmann rearrangement of oximes of methyl ketones belonging to unsaturated γ-lactone series and also to aromatic and alicyclic series. The hydrolysis with 20% sulfuric acid led to the formation of the corresponding acid and amine, and the hydrolysis with acetic and hydrochloric acids resulted in retrobeckmann rearrangement giving the initial oximes.

CALCIUM ION CHANNEL MODULATORS and USES THEREOF

Compounds of formula (I), wherein R1 is hydrogen, hydroxyl or aralkyl; R2 is an optionally substituted alkyl, aryl or heteroaryl (said substituents are selected from hydroxyl, alkoxyl, haloalkoxyl, aryl, heteroaryl, cycloalkyl, amino, monoalkylamino, dialkylamino, alkylsulphonyl, alkylsulphinyl, alkylsulphonylamino, acylamino, saturated or partially unsaturated heterocyclic groups and groups of formula COY); W is selected from oxygen, sulphur, groups of formula NR7, wherein R7 is hydrogen, alkyl, aryl or heteroaryl and groups of formula CR8R9, wherein R8 and R9 are hydrogen, alkyl, aryl or heteroaryl; and X is selected from nitrogen and groups of formula CR10, wherein R10 is hydrogen, alkyl, aryl, heteroaryl, halogen or haloalkyl, inhibit the interaction between Cavx channels and Cavβ proteins and are of use in the treatment and prevention of a number of diseases and conditions including pain and lower urinary tract disorders.

Selective hydrogenation of amides using Rh/Mo catalysts

Rh/Mo catalysts formed in situ from Rh6(CO)16 and Mo(CO)6 are effective for the liquid phase hydrogenation of CyCONH2 to CyCH2NH2 in up to 87% selectivity, without the requirement for ammonia to inhibit secondary amine formation. Use of in situ HP-FTIR spectroscopy has shown that decomposition of metal carbonyl precursors occurs during an extended induction period, with the generation of recyclable, heterogeneous, bimetallic catalysts. Variations in Mo:Rh content have revealed significant synergistic effects on catalysis, with optimum performance at values of ca. 0.6, and substantially reduced selectivities at ≥1. Good amide conversions are noted within the reaction condition regimes 50-100 bar H2 and 130-160 °C. Ex situ characterization of the catalysts, using XRD, XPS and EDX-STEM, has provided evidence for intimately mixed (ca. 2-4 nm) particles that contain metallic Rh and reduced Mo oxides, together with MoO3. Silica-supported Rh/Mo analogues, although active, perform poorly at 150 °C and deactivate during recycle.

Selective hydrogenation of amides using ruthenium/ molybdenum catalysts

Recyclable, heterogeneous bimetallic ruthenium/molybdenum catalysts, formed in situ from triruthenium dodecacarbonyl [Ru3(CO)12] and molybdenum hexacarbonyl [Mo(CO)6], are effective for the selective liquid phase hydrogenation of cyclohexylcarboxamide (CyCONH2) to cyclohexanemethylamine (CyCH2NH2), with no secondary or tertiary amine by-product formation. Variation of Mo:Ru composition reveals both synergistic and poisoning effects, with the optimum combination of conversion and selectivity at ca. 0.5, and total inhibition of catalysis evident at ≥1. Good amide conversions are noted within the reaction condition regimes 20100 bar hydrogen and 145-160°C. The order of reactivity of these catalysts towards reduction of different amide functional groups is primary > tertiary ? secondary. In situ HP-FT-IR spectroscopy confirms that catalyst genesis occurs during an induction period associated with decomposition of the organometallic precursors. Ex situ characterisation, using XRD, XPS and EDX-STEM, for active Mo:Ru compositions, has provided evidence for intimately mixed ca. 2.5-4 nm particles that contain metallic ruthenium, and molybdenum (in several oxidation states, including zero).

INDOLE- 3 -GLYOXYLAMIDE DERIVATIVES FOR USE AS CALCIUM ION CHANNEL MODULATORS

Compounds of formula (I) are of use in treating a range of conditions, including pain.