2556-73-2

Usage

Uses

Used in Chemical Industry:
N-Methylcaprolactam is used as an inhibitor for the prevention of hydrate formation in the chemical industry. This application is significant because hydrate formation can cause blockages and operational issues in pipelines and equipment, leading to decreased efficiency and potential safety hazards.
Used in Research and Development:
N-Methylcaprolactam is utilized in the study of the inhibition mechanism of poly-[N-vinylcaprolactam] (PVCAP) and its related compounds. This research is crucial for understanding the behavior of these compounds and their potential applications in various fields, such as oil and gas production, where hydrate formation is a common issue.

InChI:InChI=1/C7H13NO/c1-8-6-4-2-3-5-7(8)9/h2-6H2,1H3

Upstream product

• 105-60-2 caprolactam 
• 67-56-1 methanol 
• 77-78-1 dimethyl sulfate 
• 71-43-2 benzene 
• 2525-16-8 O-methylcaprolactim 
• 80-48-8 methyl p-toluene sulfonate 
• 74-88-4 methyl iodide 
• 1670-47-9 1,1-diethoxycyclohexane 
• 85462-16-4 N-Methyl-O-p-nitrophenylsulphonylhydroxylamine 
• 66-27-3 Methyl methanesulfonate 
• 110-71-4 1,2-dimethoxyethane 
• 3553-94-4 1-trimethylsilanyl-azepan-2-one 
• 627-93-0 hexanedioic acid dimethyl ester 
• 512-56-1 trimethyl phosphite 

Downstream Products

• 1138-06-3 5-Methylaminopentyl-phenyl-keton 
• 1192-95-6 hexahydro-1-methyl-1H-azepine 
• 26410-96-8 6-(methylamino)hexanoic acid 
• 59891-41-7 3-ethylhexahydro-1-methyl-<1H>azepin-2-one 
• 71556-70-2 hexahydro-1-methyl-3-(3-oxocyclohexen-1-yl)<2H>azepin-2-one 
• 126336-86-5 3-Methyl-N-[1-methyl-azepan-(2E)-ylidene]-benzamide 
• 126336-87-6 4-Methoxy-N-[1-methyl-azepan-(2E)-ylidene]-benzamide 
• 50529-52-7 1-[1-Methyl-azepan-(2E)-ylidene]-3-phenyl-urea 
• 71592-43-3 hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one 
• 76778-41-1 3-(3',6-dimethoxy-2-biphenyl)hexahydro-1-methyl<2H>azepin-2-one 
• 87887-07-8 3-(2-chloro-3-oxocyclohex-1-enyl)hexahydro-1-methylazepin-2-one 
• 87887-08-9 3-(2-bromo-3-oxocyclohex-1-enyl)hexahydro-1-methylazepin-2-one 
• 129941-34-0 2(S)-<(tert-butyloxycarbonyl)amino>-3-cyclohexyl-1(S)-hydroxy-1-(1-methyl-2-oxoperhydroazepin-3(S)-yl)propane 
• 126336-84-3 N-[1-Methyl-azepan-(2E)-ylidene]-benzamide 

Relevant academic research and scientific papers

Preparation of alkylated compounds using the trialkylphosphate

[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

PROCESS FOR THE SYNTHESIS OF N-SUBSTITUTED LACTAMS AND AMIDES

A process for the synthesis of N-alkylated lactams via reductive alkylation. The process of the present disclosure may be conducted by the addition of an aldehyde to a lactam in the presence of a catalyst under a reducing atmosphere.

A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines

The hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ?-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2-methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78% yield.

Copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagents

The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.

Direct conversion of polyamides to ω-hydroxyalkanoic acid derivatives by using supercritical MeOH

We examined the decomposition of polyamides such as nylon-6 and nylon-12 by using supercritical MeOH as the reaction media. The treatment of waste nylon-6 with supercritical MeOH resulted in smooth depolymerization, forming caprolactam as the first product which was then converted to a mixture of methyl 6-hydroxycapronate and methyl 5-hexenoate in a ratio of approximately 1:1. The reaction progress was traced using gas chromatography (GC) analyses, and precise product distribution was estimated. During the decomposition of nylon-6, N-methylcaprolactam and methyl 6-(N,N-dimethylamino)capronate were detected as intermediates. The sum of the all detectable products and intermediates exceeded 80%. In addition, we examined the decomposition reaction initiating from caprolactam, N-methylcaprolactam, and methyl N,N-dimethylcapronate under similar reaction conditions, and observed that the final two products were formed in similar yields and ratios. Kinetic analyses by using a simulation study based on the experimental data were performed, and kinetic parameters for each step were estimated. Nylon-12 underwent similar conversion to produce methyl 12-hydroxydodecanoate in good yield. Because methyl ω-hydroxyalkanoate is known to be an important intermediate in the chemical industry, the present method has the potential for producing valuable compounds from waste material. Thus, the first upgrade in the chemical recycling of plastics was accomplished.

PROCESS FOR PRODUCING 6-HYDROXYCAPROIC ESTER AND PROCESS FOR PRODUCING TRIALKYLAMINE

A process for producing a 6-hydroxycapoic ester and a process for producing a trialkylamine in both of which nylon-6, ε-caprolactam, which is a monomer therefore, etc. are used as a raw material. The processes are intended to make nylon-6 wastes reusable in various applications without consuming a large quantity of energy. The process for producing a 6-hydroxycarpoic ester and process for producing a tiralkylamine are characterized by reacting amide compounds basically comprising ε-caprolactam with an alcohol in a supercritical state to obtain a 6-hydroxycaproic ester and a trialkylamine.

PROCESS FOR THE PRODUCTION OF LACTAMS

A homogeneous process for the hydrogenation of dicarboxylic acid and/or derivative thereof with an amine in the presence of a catalyst comprising: (a) ruthenium or osmium; and (b) an organic phosphine; and wherein the hydrogenation is carried out in the presence of water.

Inhibitors of histone deacetylase

The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

N-(DIMETHYLALKOXYSILYLMETHYL)- AND N-(DIMETHYLARYLOXYSILYLMETHYL)LACTAMS

A comparison is made of conditions and preparative possibilities of synthesizing Si-substituted N-(dimethylsilylmethyl)lactams with oxygen-containing substituents (alkoxides, aryloxides, benzoates, and triflates) by several methods: by reactions of N-(dimethylchlorosilylmethyl)lactams with sodium alkoxides and with alcohols in the presence of triethylamine, by exchange reactions with trimethylsilyl derivatives of alcohols, phenols, benzoic and trifluoromethylsulfonic acids, and also by a one-pot technique using lactam, dimethylchloromethylchlorosilane, and triethylamine with subsequent addition to the reaction mixture of the alcohol and triethylamine. In the reaction of N-(dimethylchlorosilylmethyl)lactams with sodium alkoxides, concurrently with the replacement of halogen by an alkoxy group the Si-C bond is split to form N-methyllactams, which can also be prepared by the reaction of the initial chlorides with potassium hydroxide. According to IR spectroscopy, intramolecular O->Si coordination is observed in aryloxy-, benzoyloxy-, and trifluoromethylsulfonyloxy derivatives of N-(dimethylsilylmethyl)lactams, whereas the corresponding alkoxy derivatives lack this interaction. The structure of 1-(dimethylsilylmethyl)-2-pyrrolidone phenoxide and benzoate, 1-(dimethylpentafluorophenoxysilylmethyl)perhydro-2-azepinone, and 1-(dimethyltrifluoromethylsulfonyloxymethyl)-2-piperidone was studied by x-ray structural analysis. The lengths of the axial (C=)O->Si and Si-O bonds are, respectively, 2.367 and 1.711(2) Angstroem for the first, 2.228 and 1.711(2) Angstroem for the second, 2.078 and 1.787(2) Angstroem for the third, and 1.753 and 2.785(2) Angstroem for the fourth compound. Variations in the bond lengths are due to the properties of the Si-substituent and to the size of the lactam rings. The ease of formation of the Si-substituted N-(dimethylsilylmethyl)lactams with oxygen-containing substituents via the exchange reaction of N-(dimethylchloromethyl)lactams with the corresponding trimethylsiloxy derivatives correlates with the strength of the silicon-oxygen coordination in the reaction products.