4542-47-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Morpholino)propionitrile is used as a chemical intermediate for the synthesis of various drugs and pharmaceuticals. Its presence in the molecular structure of target compounds allows for the development of new therapeutic agents with potential applications in treating a range of medical conditions.
Used in Chemical Production:
3-(4-Morpholino)propionitrile is utilized as a precursor in the production of other chemicals and materials. Its reactivity and functional groups make it a valuable component in the synthesis of a variety of chemical products, contributing to the diversity of applications in different industries.
Used in Biological and Pharmacological Research:
3-(4-Morpholino)propionitrile is studied for its potential biological and pharmacological properties, such as anti-inflammatory and antiviral activities. This research aims to explore its therapeutic potential and identify new applications in medicine, possibly leading to the development of novel treatments for inflammatory and viral diseases.
While the provided materials do not specify different industries for the uses of 3-(4-Morpholino)propionitrile, the above applications cover its primary roles in the pharmaceutical and chemical industries, as well as its potential in biological and pharmacological research.

InChI:InChI=1/C7H12N2O/c8-2-1-3-9-4-6-10-7-5-9/h1,3-7H2

Upstream product

• 110-91-8 morpholine 
• 542-76-7 3-Chloropropionitrile 
• 110-67-8 3-Methoxypropionitrile 
• 107-13-1 acrylonitrile 
• 109-78-4 3-Hydroxypropionitrile 

Downstream Products

• 20120-24-5 ethyl 3-morpholinopropionate 
• 77283-38-6 N-acetyl-sulfanilic acid-(3-morpholino-propylamide) 
• 77837-45-7 sulfanilic acid-(3-morpholino-propylamide) 
• 30077-72-6 3-(3,4-dimethoxy-phenyl)-2-morpholin-4-ylmethyl-acrylonitrile 
• 32834-99-4 2-morpholin-4-ylmethyl-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile 
• 30077-81-7 3-morpholino-5-(3',4',5'-trimethoxybenzyl)acrylopyrimidine 
• 83166-73-8 5-(3-iodo-4,5-dimethoxy-benzyl)-pyrimidine-2,4-diamine 

Relevant academic research and scientific papers

Arylsulfochlorination of β-aminopropioamidoximes giving 2-aminospiropyrazolylammonium arylsulfonates

The reaction of P-(morpholin-1-yl)propioamidoxime with aromatic sulfonyl chlorides (p-XC6H4SO2Cl; X = CH3O, CH3, H, Br, Cl, NO2) in chloroform in the presence of triethyl-amine does not produce expected O-arylsulfonyl-β-(morpholin-1-yl)propioamidoximes; instead, this reaction affords isomers of the latter compounds, 2-amino-8-oxa-l,5-diazaspiro[4.5]dec-1-ene-5-ammonium arylsulfonates. The structures of the reaction products were established by physicochemical methods, spectroscopy, and X-ray diffraction.

New asymmetrical morpholinium- and 1,1-dioxidothiomorpholinium-based dicationic ionic liquid: structure, thermophysical and electrochemical properties of propylene carbonate solutions

A new asymmetrical 1,1-dioxidothiomorpholinium- and morpholinium-based dicationic ionic liquid (4-ethyl-4-[3-(4-ethyl-1,1-dioxidothiomorpholin-4-ium-4-yl)propyl]morpholin-4-ium tetrafluoroborate (EtDTMC3EtM·2BF4)) was synthesized in four stages and characterized by 1H, 13C, 1H,1H–COSY NMR, single X-ray diffraction, XPS spectroscopy and simultaneous thermal analysis. Electrical conductivities of several EtDTMC3EtM·2BF4 solutions in propylene carbonate (PC) were measured in the 298 – 368 K temperature range and analyzed using the Arrhenius, Litovitz, and Vogel–Fulcher–Tammann (VFT) equations.

Ruthenium (II) β-diketimine as hydroamination catalyst, crystal structure and DFT computations

A new half-sandwich ruthenium (II) complex containing β-diketiminate ligand has been synthesized and used for hydroamination of acrylonitrile with aromatic and aliphatic amines. The catalytic activity of prepared complex was compared with a series of ruthenium complexes of β-diketiminate ligands, and the effect of electronic and steric properties of these ligands on catalytic activity of their complexes was investigated. Replacement of H atom in α position of β-diketiminate with (CF3) as an electron-withdrawing group leads to decreasing the reaction yield, and on the other hand, electron-donating group (CH3) has the opposite effect. In addition, crystal structure of [Ru(p-cymen)Cl(LH,Cl)] was determined by single X-ray crystallography. Hirshfeld surface analysis has been performed to determine the dominate interactions in molecular crystal. Furthermore, density functional, QTAIM and energy calculations have been carried out, to get the detailed insight into electronic and bonding characteristics of titled compound.

Bio-heterogeneous Cu(0)NC@PHA for n-aryl/alkylation at room temperature

A pure cellulose was derived from waste fibre and it was chemically modified to a hydroxamic acid ligand. The poly(hydroxamic acid) was treated with an aqueous copper solution to afford the greenish stable five-membered copper complex; namely Cu(II)@PHA. Further, the Cu(II)@PHA was treated with a reducing agent hydrazine hydride to give brown colour cellulose supported copper nanocomplex (Cu(0)NC@PHA). The Cu(0)NC@PHA was characterised by ATR-FTIR, FE-SEM & EDS, TEM, ICP-OES, TGA, XRD and XPS analyses. The cellulose-based Cu(0)NC@PHA was used for the n-aryl/alkylation (Michael addition) reaction with a variety of α,β-unsaturated Michael acceptors to produce the corresponding n-aryl/alkyl products with an excellent yield at room temperature. The Cu(0)NC@PHA showed extraordinary stability and it was easily filtered out from the reaction mixture and may potentially recycled up to five times without loss of its original catalytic ability.

Inhibitor design to target a unique feature in the folate pocket of Staphylococcus aureus dihydrofolate reductase

Staphylococcus aureus (Sa) is a serious concern due to increasing resistance to antibiotics. The bacterial dihydrofolate reductase enzyme is effectively inhibited by trimethoprim, a compound with antibacterial activity. Previously, we reported a trimethoprim derivative containing an acryloyl linker and a dihydophthalazine moiety demonstrating increased potency against S. aureus. We have expanded this series and assessed in vitro enzyme inhibition (Ki) and whole cell growth inhibition properties (MIC). Modifications were focused at a chiral carbon within the phthalazine heterocycle, as well as simultaneous modification at positions on the dihydrophthalazine. MIC values increased from 0.0626–0.5 μg/mL into the 0.5–1 μg/mL range when the edge positions were modified with either methyl or methoxy groups. Changes at the chiral carbon affected Ki measurements but with little impact on MIC values. Our structural data revealed accommodation of predominantly the S-enantiomer of the inhibitors within the folate-binding pocket. Longer modifications at the chiral carbon, such as p-methylbenzyl, protrude from the pocket into solvent and result in poorer Ki values, as do modifications with greater torsional freedom, such as 1-ethylpropyl. The most efficacious Ki was 0.7 ± 0.3 nM, obtained with a cyclopropyl derivative containing dimethoxy modifications at the dihydrophthalazine edge. The co-crystal structure revealed an alternative placement of the phthalazine moiety into a shallow surface at the edge of the site that can accommodate either enantiomer of the inhibitor. The current design, therefore, highlights how to engineer specific placement of the inhibitor within this alternative pocket, which in turn maximizes the enzyme inhibitory properties of racemic mixtures.

Efficient protocol for Aza-Michael addition of N-heterocycles to α,β-unsaturated compound using [Ch]OH and [n-butyl urotropinium]OH as basic ionic liquids in aqueous/solvent free conditions

The present work emphasizes on a green methodology using designed and synthesized basic ionic liquid, [n-butyl Urotropinium]OH, and commercially available aqueous solution of choline hydroxide [Ch]OH as catalysts for executing Aza-Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature. The highlighting features of these catalysts include using low concentration of both catalysts along with [Ch]OH being low cost and biodegradable, [n-butyl Urotropinium]OH significantly enhancing the high substrate/catalyst ratio to obtain the desired products in high yield and purity in most cases. Further, both catalysts were recyclable and recoverable up to five cycles.

Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents

A general preparation of polyfunctional hydroxylamine benzoates from the corresponding secondary amines is reported. This convenient synthesis allows the setup of a late-stage functionalization of various secondary amines, including pharmaceuticals and peptidic derivatives. Thus, a cross-coupling of hydroxylamine benzoates with various alkyl-, aryl-, and heteroaryl-zinc chlorides in the presence of 5 mol % CoCl2 (25 °C, 2 h) provides a range of polyfunctional tertiary amines. This method was used to prepare penfluridol and gepirone.

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.

TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole

TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.

Palladium nanocatalysts in glycerol: Tuning the reactivity by effect of the stabilizer

Palladium nanoparticles (PdNPs) prepared in neat glycerol containing TPPTS (tris(3-sulfophenyl)phosphine trisodium salt) or cinchona-based alkaloids (cinchonidine, quinidine) as capping agents, were applied as catalysts in fluoride-free Hiyama couplings and conjugate additions with the aim of evaluating the influence of the stabilizer in the catalytic reactivity. Therefore, PdNPs stabilized by phosphine favored C–C cross-couplings, whereas those containing alkaloids showed enhanced suitability for C–C homo-couplings and conjugate additions. The metal/stabilizer coordination mode, i.e. Pd–P dative bond and π-π interaction between quinoline moiety and palladium surface, is certainly key for the stabilization of different active metallic species and then promoting distinctive catalytic pathways.