86010-68-6

Usage

Uses

Used in Pharmaceutical Industry:
N-((4-FLUOROPHENYL)METHYL)ETHANAMIDE is used as an impurity in Pimavanserin (P441800) for the treatment of Parkinson’s disease and psychosis. Its presence, although as an impurity, is significant in the context of the drug's formulation and efficacy.
Used in Organic Chemistry:
N-((4-FLUOROPHENYL)METHYL)ETHANAMIDE is used as a reagent in organic chemical oxidation reactions. Its chemical properties make it a valuable component in facilitating specific types of chemical transformations, contributing to the synthesis of various organic compounds.

Upstream product

• 103-84-4 Acetanilid 
• 60-35-5 acetamide 
• 459-57-4 4-fluorobenzaldehyde 
• 74-90-8 hydrogen cyanide 
• 456-22-4 4-Fluorobenzoic acid 
• 459-56-3 4-fluorobenzylic alcohol 
• 75-05-8 acetonitrile 
• 64-19-7 acetic acid 
• 140-75-0 para-fluorobenzylamine 
• 352-32-9 p-fluorotoluene 
• 75-36-5 acetyl chloride 

Downstream Products

• 103-84-4 Acetanilid 
• 35103-34-5 N-(p-methoxybenzyl)acetamide 
• 162401-03-8 N-(4-fluorobenzyl)ethanamine 
• 86010-70-0 N-(4-fluorobenzyl)-N-methylacetamide 
• 74554-78-2 N-acetyl-4-fluorobenzamide 

Relevant academic research and scientific papers

Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis

Recent years have witnessed important progress in synthetic strategies exploiting the reactivity of carbocations via photochemical or electrochemical methods. Yet, most of the developed methods are limited in their scope to certain stabilized positions in molecules. Herein, we report a metal-free system based on the iodine (I/III) catalytic manifold, which gives access to carbenium ion intermediates also on electronically disfavored benzylic positions. The unusually high reactivity of the system stems from a complexation of iodine (III) intermediates with BF3. The synthetic utility of our decarboxylative Ritter-type amination protocol has been demonstrated by the functionalization of benzylic as well as aliphatic carboxylic acids, including late-stage modification of different pharmaceutical molecules. Notably, the amination of ketoprofen was performed on a gram scale. Detailed mechanistic investigations by kinetic analysis and control experiments suggest two mechanistic pathways.

C-H Amination via Electrophotocatalytic Ritter-Type Reaction

A method for C-H bond amination via an electrophotocatalytic Ritter-Type reaction is described. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion in an electrochemical cell under irradiation. These conditions convert benzylic C-H bonds to acetamides without the use of a stoichiometric chemical oxidant. A range of functionality is shown to be compatible with this transformation, and several complex substrates are demonstrated.

Reductive Amidation without an External Hydrogen Source Using Rhodium on Carbon Matrix as a Catalyst

An efficient method for preparation of secondary amides from primary amides and aldehydes using rhodium on carbon matrix as catalyst was developed. The method does not require any external hydrogen source and carbon monoxide is used as a reducing agent. The most active rhodium catalysts were characterized by BET, TEM and XPS techniques. Unexpectedly, it was found that heterogeneous rhodium on carbon matrix works as precatalyst for homogenous active species due to leaching of rhodium to the solution. Various secondary amides were synthesized and checked for antifungal activity. 4-Methoxy-N-(4-methoxybenzyl)benzamide demonstrated promising activity against Rhizoctonia Solani.

Transition-Metal- and Halogen-Free Oxidation of Benzylic sp 3 C-H Bonds to Carbonyl Groups Using Potassium Persulfate

Aryl carbonyl compounds including acetophenones, benzophenones, imides, and benzoic acids are prepared from benzyl substrates using potassium persulfate as oxidant with catalytic pyridine in acetonitrile under mild conditions. Neither transition metals nor halogens are involved in the reactions.

Dichotomy of Atom-Economical Hydrogen-Free Reductive Amidation vs Exhaustive Reductive Amination

Rh-catalyzed one-step reductive amidation of aldehydes has been developed. The protocol does not require an external hydrogen source and employs carbon monoxide as a deoxygenative agent. The direction of the reaction can be altered simply by changing the solvent: reaction in THF leads to amides, whereas methanol favors formation of tertiary amines.

A lewis acid-promoted pinner reaction

Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction.

Benzyl amide-ketoacid inhibitors of HIV-integrase

Integrase is one of three enzymes expressed by HIV and represents a validated target for therapy. Previous reports have demonstrated that the diketoacid-based chemotype is a useful starting point for the design of inhibitors of this enzyme. In this study, one of the ketone groups is replaced by a benzylamide resulting in a new potent chemotype. A preliminary SAR study is carried out to investigate the substitution requirements on the phenyl ring and methylene group of the benzylamide.

Catalytic metathesis of simple secondary amides

(Chemical Equation Presented) Trading places: The metathesis of secondary amides through a transacylation mechanism has been achieved by employing catalytic quantities of an organic imide and a Bronsted base (see scheme). Equilibrium-controlled exchange between various amide pairs is demonstrated for substrates bearing N-alkyl and N-aryl substituents.

ORTHO-SUBSTITUTED BENZOIC ACID DERIVATIVES FOR THE TREATMENT OF INSULIN RESISTANCE

The present invention provides a compound of formula (I), wherein n is 0, 1 or 2; R1 represents halo, a C1-4alkyl group which is optionally substituted by one or more fluoro, a C1-4alkoxy group which is optionally substitu

Reactions of Thianthrene Cation Radical with Acyclic and Cyclic Alcohols

Thianthrene cation radical perchlorate (Th(.+)*ClO4(-)) reacted readily with cycloalkanols (C5, C7, C8, and C12), alkan-2-ols (C3, C5, C6, and C8), 3-hexanol, neopentyl alcohol, a number of benzyl alcohols, dl- and (S)-1-phenylethanol, cyclopentyl- and cyclohexylmethanols, the exo- and endo-borneols, and norborneols.Reactions were carried out with an excess of the alcohol in acetonitrile solution containing 2,6-di-tert-butyl-4-methylpyridine.Products were alkenes, ethers, and N-substituted acetamides, depending on the structure of the alcohol.Thianthrene (Th) and its 5-oxide (ThO) were formed in equal amounts.The sum of amounts of products from the alcohol was equal to the amount of ThO.All reactions are interpretable on the basis of the ultimate formation and further reactions of a 5-alkoxythianthreniumyl ion (ROTh(+)).The predominant formation of nortricyclene from the norborneols is striking and is discussed.Swern-Moffatt-type oxidations of the alcohols were not observed.