31991-78-3

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-benzamidobutyl)benzamide is used as a pharmaceutical intermediate for the synthesis of various drugs and chemicals. Its structural properties allow it to serve as a building block in the creation of new therapeutic agents, contributing to the development of novel treatments for a range of medical conditions.
Used in Drug Development Research:
In the realm of research and development, N-(4-benzamidobutyl)benzamide is utilized to explore its interactions with biological systems, potentially leading to the discovery of new pharmaceuticals and therapeutic agents. Its ability to engage with receptors makes it a valuable tool in understanding and manipulating biological processes for medicinal purposes.

Upstream product

• 3440-28-6 N-benzoyl-beta-alanine 
• 5692-23-9 N-(4-aminobutyl)benzamide 
• 98-88-4 benzoyl chloride 
• 110-60-1 1,4-diaminobutane 
• 13645-31-3 1,2-dibenzoyl-hexahydro-pyridazine 
• 7646-66-4 N-benzoylaziridine 
• 55-21-0 benzamide 
• 13435-07-9 N,N'-bis-(trimethylsilyl)-1,4-butanediamine 
• 99422-98-7 NN'-di(isobutylidene)-1,4-diaminobutane 
• 6970-47-4 N¹,N²-dibenzylidenebutane-1,4-diamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 120-12-7 anthracene 
• 15647-47-9 5-benzoylaminopentanoic acid 
• 100253-61-0 5-benzoylamino-valeric acid amide 

Downstream Products

• 110-52-1 1,4-dibromo-butane 
• 5692-23-9 N-(4-aminobutyl)benzamide 
• 6345-94-4 N-(4-chlorobutyl)benzamide 
• 110-60-1 1,4-diaminobutane 
• 110-56-5 1,4-dichlorobutane 
• 31719-05-8 N,N'-dibenzylbutane-1,4-diamine 
• 32039-04-6 N-Benzoyl-N'-benzyl-putrescin 
• 16012-03-6 N,N'-Dimethyl-N,N'-dibenzoyl-1,4-diaminobutan 
• 100-47-0 benzonitrile 
• 93-58-3 benzoic acid methyl ester 

Relevant academic research and scientific papers

One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70%) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65%) was obtained with 1,4-diaminobenzene as coupling amine, at 100°C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.

Microwave-assisted catalytic method for a green synthesis of amides directly from amines and carboxylic acids

Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.

Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2-CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated from the latter amides, namely RCONHCHO. Also, the anodic process was found to be more efficient with C felt as the anode, and in a mixture of 1:1 methanol/acetonitrile co-solvents.

N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: Highly selective and efficient reagents for acylation of amines in water

A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a-e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.

CDI-mediated monoacylation of symmetrical diamines and selective acylation of primary amines of unsymmetrical diamines

A highly efficient and green protocol for monoacylation of symmetrical diamines and chemoselective acylation of primary amines of unsymmetrical diamines has been developed.

Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors

Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.

Inclusion compound of β-cyclodextrin with binuclear guests containing residues of some pharmocologically important aromatic monocarboxylic acids

Stable monomeric and dimeric inclusion compounds of β-cyclodextrin with binuclear guests containing the residues of some pharmacologically important aromatic monocarboxylic acids were obtained. Pleiades Publishing, Ltd., 2011.

Imidazole-catalyzed monoacylation of symmetrical diamines

Figure Presented. An imidazole-catalyzed protocol for monoacylation of symmetrical diamines has been developed. The protocol gave selective monoacylation of aliphatic (cyclic and acyclic) primary and secondary diamines. In the reaction, imidazole acts as both catalyst and a leaving group. Different monoacylated piperazines and other diamines were synthesized at room temperature in an ethanol/water solvent system.

Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron

(Equation presented) Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.

Aziridines. 76: Neglected aspects of anthracenide (anthracenidyl) chemistry - Reactions with two N-benzoylaziridines

Reaction of anthracenide A.- with N-benzoylaziridines 1a,b forms charged radicals 3a,b by single electron transfer and homolytic ring opening. Reactions follow that are known or expected as e.g. coupling with position 9 of A.- forming dihydroanthracene anions 9a,b that yield amidoethylated dihydroanthracenes 10a,b, or react with 1a,b giving finally 9,10-bis-amidoethylated dihydroanthracenes 11a,b. Results depend on experimental conditions and on the counter ions Na+ or Li+. Coupling is not regiospecific: contributions by positions 2 and 1 reach 29% or 4%, respectively, of total coupling with the primary radical 3a; much higher contributions are possible with Li. Product 21s (probably 3,3′-disubstituted tetrahydrobianthryl) may arise by hydrogen detachment from the first intermediate (29) of coupling with position 2 and dimerization of the formed 2-substituted A.- (30). Coupling products may be fully aromatized or may be hydroxylated in one of the benzylic positions. With counter ion Li+ a non-SET reaction of 1a with the dimer of A.- is indicated by the isolation of 9-benzoyl-dihydroanthracene 15 and by 19% yield of 16a (aromatized 10a). Reaction of 3b with anthracene is indicated by 10,10′-disubstituted tetrahydrobianthryl 37. Wiley-VCH Verlag GmbH, 2000.