3480-59-9

Usage

Uses

Used in Pharmaceutical Synthesis:
N-(1-phenylethyl)benzamide is utilized as an intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity. Its ability to form amides and its presence in the synthesis of other organic compounds make it a key component in the development of new drugs.
Used in Medicine and Drug Development:
In the field of medicine and drug development, N-(1-phenylethyl)benzamide is used as a precursor for creating compounds with potential therapeutic applications. Its biological activities, including analgesic and anti-inflammatory properties, position it as a candidate for further research into treatments for pain and inflammation-related conditions.
Used in Research and Development:
N-(1-phenylethyl)benzamide is also employed in research and development settings to explore its potential applications and to understand its interactions with biological systems. This knowledge can contribute to the advancement of pharmaceutical formulations and the discovery of new therapeutic agents.

InChI:InChI=1/C15H15NO/c1-12(13-8-4-2-5-9-13)16-15(17)14-10-6-3-7-11-14/h2-12H,1H3,(H,16,17)

Upstream product

• 2902-69-4 2,2,2-trichloroacetophenone 
• 618-36-0 rac-methylbenzylamine 
• 98-85-1 1-Phenylethanol 
• 100-47-0 benzonitrile 
• 10387-93-6 N-(methoxy(phenyl)methyl)benzamide 
• 917-54-4 methyllithium 
• 65-85-0 benzoic acid 
• 7007-15-0 3-benzoyl-1,3-oxazolidin-2-one 
• 100-42-5 styrene 
• 55-21-0 benzamide 
• 98-88-4 benzoyl chloride 
• 93-99-2 benzoic acid phenyl ester 
• 213327-28-7 N-benzoyl-N-(2-fluoro-phenyl)-benzamide 
• 213327-30-1 N-benzoyl-N-(2-bromo-phenyl)-benzamide 

Downstream Products

• 64551-86-6 N-[1-phenylethyl]benzenecarbothioamide 
• 16114-84-4 Diphenylphosphinsaeure-1-diphenylphosphinyl-benzylester 
• 3480-59-9 (S)-N-(1-phenylethyl)benzamide 
• 20826-48-6 (R)-N-(1-phenylethyl)benzamide 
• 3193-62-2 N-benzyl-1-phenylethylamine 
• 17480-71-6 N-benzylidene-α-methylbenzylamine 
• 241819-55-6 1-phenyl-N-(1-phenylethyl)but-3-en-1-amine 
• 55-21-0 benzamide 
• 1256846-42-0 2-(1-phenylethyl)benzo[d][1,2]selenazol-3(2H)-one 
• 100969-25-3 N-nitroso-N-((S)-1-phenyl-ethyl)-benzamide 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 

Relevant academic research and scientific papers

Cage-like Fe,Na-Germsesquioxanes: Structure, Magnetism, and Catalytic Activity

A series of four unprecedented heterometallic metallagermsesquioxanes were synthesized. Their cage-like architectures have a unique type of molecular topology consisting of the hexairon oxo {Fe6O19} core surrounded in a triangular manner by three cyclic germoxanolates [PhGe(O)O]5. This structural organization induces antiferromagnetic interactions between the FeIIIions through the oxygen atoms. Evaluated for this first time in catalysis, these compounds showed a high catalytic activity in the oxidation of alkanes and the oxidative formation of benzamides from alcohols.

AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS

The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.

Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow

Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i

Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(ii) carboxylates

Reactions that enable carbon–nitrogen, carbon–oxygen and carbon–carbon bond formation lie at the heart of synthetic chemistry. However, substrate prefunctionalization is often needed to effect such transformations without forcing reaction conditions. The development of direct coupling methods for abundant feedstock chemicals is therefore highly desirable for the rapid construction of complex molecular scaffolds. Here we report a copper-mediated, net-oxidative decarboxylative coupling of carboxylic acids with diverse nucleophiles under visible-light irradiation. Preliminary mechanistic studies suggest that the relevant chromophore in this reaction is a Cu(ii) carboxylate species assembled in situ. We propose that visible-light excitation to a ligand-to-metal charge transfer (LMCT) state results in a radical decarboxylation process that initiates the oxidative cross-coupling. The reaction is applicable to a wide variety of coupling partners, including complex drug molecules, suggesting that this strategy for cross-nucleophile coupling would facilitate rapid compound library synthesis for the discovery of new pharmaceutical agents. [Figure not available: see fulltext.].

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.

Tropylium-promoted Ritter reactions

The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Direct enantioseparation of axially chiral 1,1′-biaryl-2,2′-diols using amidine-based resolving agents

Amidine-based optically active resolving agents for enantiomer separation of axially chiral 1,1′-biaryl-2,2′-diols have been developed. A strongly basic amidine bearing no substituents on its nitrogen atoms enables the formation of their diastereomeric salts upon being mixed with weakly acidic phenol derivatives. Enantiopure 1,1′-biaryl-2,2′-diols can be obtained in high yields after only one crystallization of their salts with the chiral amidine derived from dehydroabietic acid. X-ray crystallography revealed that the amidine moiety forms a salt with the phenol group and additional intermolecular NH/π interactions contribute to the efficient chiral recognition process.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.