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Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Fluorobenzyl)morpholine is used as an intermediate in the synthesis of pharmaceuticals for its ability to modulate various biological processes. The presence of the 4-fluorobenzyl group allows for the fine-tuning of drug properties, potentially leading to the development of more effective medications.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-(4-Fluorobenzyl)morpholine is utilized as an intermediate in the creation of compounds designed to protect crops and enhance agricultural productivity. Its unique structural features can contribute to the development of novel agrochemicals with improved performance and selectivity.
Used in Medicinal Chemistry Research:
4-(4-Fluorobenzyl)morpholine is employed as a valuable building block in medicinal chemistry research. Its structural attributes, including the morpholine ring, offer opportunities for the design of new pharmaceutical agents with optimized pharmacokinetic properties, potentially leading to safer and more effective treatments.

Upstream product

• 110-91-8 morpholine 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 502-00-1 p-fluorobenzyl acetate 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 3859-77-6 toluene-4-sulfonic acid-(4-fluoro-benzyl ester) 
• 352-32-9 p-fluorotoluene 
• 459-46-1 4-Fluorobenzyl bromide 
• 1233656-32-0 C₁₆H₁₈FO₄P 
• 459-56-3 4-fluorobenzylic alcohol 

Relevant academic research and scientific papers

Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis

Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of several types of pharmaceuticals, a new procedure that relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range of substrates can be used under mild conditions, leading to high chemical yields of the desired secondary and tertiary amines.

Continuous photochemical benzylic bromination using: In situ generated Br2: Process intensification towards optimal PMI and throughput

The detailed development of photochemical benzylic brominations using a NaBrO3/HBr bromine generator in continuous flow mode is reported. Optimization of the bromine generator enables highly efficient mass utilization by HBr recycling, coupled with fast interphase transfer within a microstructured photochemical reactor (405 nm LEDs). Intensification of the reaction system, including complete removal of organic solvent, allowed a reduction in PMI from 13.25 to just 4.33. The photochemical transformation achieved exceptionally high throughput, providing complete conversion in residence times as low as 15 s. The organic solvent-free preparation of two pharmaceutically relevant building blocks was demonstrated with outstanding mass efficiency, by monobromination (1.17 kg scale in 230 min, PMI = 3.08) or dibromination (15 g scale in 20 min, PMI = 3.64).

A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging

Translation of new 18F-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for 18F-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful 18F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [18F]fluoride of human doses of [18F]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [18F]5-fluorouracil precursor. Routine production of >10 mCi doses of [18F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [18F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated 18F-fluorination.

Base-promoted N-alkylation using formamides as the N-sources in neat water

An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.

Highly efficient amination in neat water of benzyl chlorides with dialkylformamides catalysed by N-heterocyclic carbene-palladium(II)-1- methylimidazole complex

Dialkylformamides are excellent N-sources in the amination of benzyl chlorides when catalysed by a NHC-Pd(II)-Im complex. In the presence of NaOH and the catalyst, variously substituted benzyl chlorides and five different dialkylformamides reacted smoothly to afford the corresponding N,N-dialkyl-benzylamines in good to almost quantitative yields in eco-friendly solvent water at 50 °C within 3 h.

ROMP-derived oligomeric phosphates for application in facile benzylation

The development of new ROMP-based oligomeric benzyl phosphates (OBP n) is reported for use as soluble, stable benzylating reagents. These oligomeric reagents are readily synthesized from commercially available materials and conveniently polymerized and purified in a one-pot process, affording bench-stable, pure white, free-flowing solids on multigram scale. Utilization in benzylation reactions with a variety of nucleophiles is reported.

Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

The palladium complex prepared in situ from [Pd(η3-C3H5)(cod)]BF4 and bidentate phosphine DPPF was a good catalyst for the nucleophilic substitution of benzyl acetate. Significant acceleration of the palladium-catalyzed substitution was observed when an alcohol was employed as a reaction solvent. The palladium catalyst was effective for the benzylation of various stabilized carbanions, amines, and benzenesulfinate with benzylic acetates.

Catalytic amination of aldehydes to amides

Aldehydes react in a disproportionation reaction in the presence of rhodium catalysts to yield amines and amides. By adding N-methylmorpholine N-oxide as an oxidant in the presence of catalytic amounts of rhodium, the oxidative amination of aldehydes proceeds selectively to give the corresponding amide. Both aliphatic and aromatic aldehydes react with secondary amines to yield carboxylic acid amides in good to excellent yields.

Use of polymer supported reagents for clean multi-step organic synthesis: Preparation of amines and amine derivatives from alcohols for use in compound library generation

The automated sequential application of polymer supported perruthenate (PSP) and polymer supported cyanoborohydride (PSCBH) in an oxidation-reductive amination procedure allowed the efficient transformation of simple alcohols into more complex amines which can be further derivatised by the use of polymer bound amino sulfonylpyridinium chlorides.

N-2-hydroxyethyl N'-alkylpiperazines and benzylamines: Chemistry and pharmacology

The authors have prepared some benzylamine derivatives and established a structure-antidysrhythmic activity relationship. Most of the compounds exhibited significant activity. One also showed interesting anticalcium activity.