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

• 618-36-0 rac-methylbenzylamine 
• 7007-15-0 3-benzoyl-1,3-oxazolidin-2-one 
• 32366-25-9 1-azidoethylbenzene 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 98-85-1 1-Phenylethanol 
• 55-21-0 benzamide 
• 35474-20-5 N-chloro-α-methylbenzylamine 
• 108-88-3 toluene 
• 591-50-4 iodobenzene 
• 120-46-7 1,3-diphenylpropanedione 
• 13437-79-1 (α)-methylbenzylamine hydrochloride 
• 100-51-6 benzyl alcohol 
• 959-22-8 p-nitrophenylbenzoate 
• 585-71-7 (1-bromoethyl)benzne 

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 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 100-47-0 benzonitrile 
• 1297595-41-5 (S)-N-(1-phenylethyl)benzimidoyl chloride 
• 100969-25-3 N-nitroso-N-((S)-1-phenyl-ethyl)-benzamide 

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.].

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%.

Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides

A nickel-catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α-arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS-CoV PLpro inhibitors, and KCNQ channel openers.

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.

Design and synthesis of 3,3′-triazolyl biisoquinoline N,N’-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles

A new strategy to effectively lock the conformation of substituents at the 3,3′-positions of axial-chiral biisoquinoline N,N’-dioxides was developed based on the strong dipole–dipole interaction between 1,2,3-triazole and pyridine N-oxide rings. The crystal structure and the DFT calculations of 3,3′-bis(1-benzyl-1H-1,2,3-triazole-4-yl)-1,1′-biisoquinoline N,N’-dioxide (3a) provided strong support for this strategy. Furthermore, we successfully demonstrated that readily available 4-trimethylsilyl-1,2,3-triazoles are viable nucleophiles for Hiyama cross-coupling.

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).

Carboxyesterase polypeptides for amide coupling

The present invention provides engineered carboxyesterase enzymes having improved properties as compared to a naturally occurring wild-type carboxyesterase enzymes, as well as polynucleotides encoding the engineered carboxyesterase enzymes, host cells capable of expressing the engineered carboxyesterase enzymes, and methods of using the engineered carboxyesterase enzymes in amidation reactions.