Morpholine

Manufactured by Merck Group

Sourced in United States, Italy

Morpholine is a heterocyclic organic compound with the chemical formula C4H9NO. It is a colorless, hygroscopic liquid with a characteristic amine odor. Morpholine is used as a chemical intermediate and a solvent in various industrial applications.

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Spelling variants of this product

Morpholine ethanesulfonic acid (3 citations) 4-methyl-morpholine borane (2 citations) MOPS – [3- (N-morpholine) propanesulfonic acid] (2 citations)

22 protocols using morpholine

Synthesis and Characterization of Sulfonamides

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All the solvents used were analytically pure. The reagents 5-isopropyl-2-methylphenol (carvacrol), chlorosulfonic acid, morpholine, 4-fluoroaniline, pyridin-2-yl methanamine, 2-hydroxyaniline, 2,4-dichloroaniline were obtained from Sigma Aldrich.
The synthesis sulfonamides S1–S5, as already described in the literature (de Oliveira et al., 2016 (link)) was performed in two steps: firstly, the synthesis of 4-hydroxy-2-isopropyl-5-methylbenzene-1-sulfonyl chloride (ChS) was performed, subsequently, the ChS was used in reactions with different amines (Scheme 1). ChS was obtained from the reaction of carvacrol to six equivalents of chlorosulfonic acid. The sulfonamides obtained in this study were prepared from ChS with two equivalents of amine added slowly. Reactions were followed by thin layer chromatography (TLC). All sulfonamides were purified by acid-base extraction and the compounds were duly characterized by spectroscopic and spectrometric techniques.

de Oliveira A.S., Llanes L.C., Nunes R.J., Nucci-Martins C., de Souza A.S., Palomino-Salcedo D.L., Dávila-Rodríguez M.J., Ferreira L.L., Santos A.R, & Andricopulo A.D. (2021). Antioxidant Activity, Molecular Docking, Quantum Studies and In Vivo Antinociceptive Activity of Sulfonamides Derived From Carvacrol. Frontiers in Pharmacology, 12, 788850.

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Synthesis of 4-(Phenylsulfonyl)morpholine

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The precursor’s benzenesulfonyl chloride and morpholine were purchased commercially from Sigma–Aldrich (St. Louis, USA). The precursors were used without further purification. The title compound 4-(Phenylsulfonyl) morpholine was prepared by reaction of 1 equivalent of benzenesulfonyl chloride (1 mmol) and morpholine (2 mmol) in methanolic mixture of pyridine (5 mL) at low temperature (∼0 °C) under stirring by 2 h as a previously described procedure (Buchmann and Schalinatus, 1962 ). The material thus formed was filtered and washed with methanol solution then dried. The resulting material was recrystallized by using heating methanol solution. The crystals were formed by slow solvent evaporation at room temperature. The complete structure elucidation was confirmed by NMR ¹H and ¹³C spectroscopy analysis by comparison with literature data (Modarresi-Alam et al., 2009 (link)). The NMR spectra in CDCl₃, were recorded in Varian-Mercury 300 (300 MHz for ¹H and 75 MHz for ¹³C) spectrometer, using tetramethylsilane (TMS) as internal standard. Analytical Data: ¹H RMN (CDCl₃, 300 MHz): t (4H; 3.01 ppm); t (4H; 3.74 ppm); t (2H, J = 7.56 Hz); t (1H; 7.64 ppm); d (2H; 7.77 ppm) ¹³C RMN (CDCl₃, 75 MHz): δ = 46; 66.10; 127.85; 129.15; 133.09; 135.13. The synthesis is described by the scheme present in Fig. 1.

Oliveira M.T., Teixeira A.M., Cassiano C.J., Sena DM J.r., Coutinho H.D., Menezes I.R., Figueredo F.G., Silva L.E., Toledo T.A, & Bento R.R. (2015). Modulation of the antibiotic activity against multidrug resistant strains of 4-(phenylsulfonyl) morpholine. Saudi Journal of Biological Sciences, 23(1), 34-38.

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Characterization of Indole Derivatives

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Example 3

General information: ¹H NMR spectra were recorded on a Bruker Avance III600 instrument, in deuterated solvents and were referenced to TMS (6 scale). Flash chromatography was performed on Merck silica gel 60 (0.040-0.063 mm). Analytical thin layer chromatography (TLC) was carried out on precoated (0.25 mm) Merck silica gel F-254 plates. Mass spectra were recorded with a LTQ Orbitrap Discovery instrument, possessing an Ionmax ionization source. 3-Acetoxyindole, 5-bromoindole, 6-chloroindole, 5-cyanoindole, methyl indole-5-carboxylate, methyl indole-6-carboxylate, 5-methylindole, iodine, potassium iodide, thiophenol, oxalyl chloride, anhydrous aluminum chloride, hydroxylamine hydrochloride, anhydrous pyridine, triethylamine, 1,2-dibromoethane, piperazine and morpholine were purchased from Sigma-Aldrich. Anhydrous dichloromethane and anhydrous N,N-dimethylformamide were purchased from Acros organics.

US11213510B2. Thioindirubins (2022-01-04). City of Hope [US], National and Kapodistrian University of Athens [GR]. Inventors: Sangkil Nam [US], David Horne [US], Ravi Salgia [US], Alexios Leandros Skaltsounis [GR], Nicolas Gaboriaud-Kolar [GR], Panagiotis Gerolymatos [GR], Nikolaos Lougiakis [GR].

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Synthesis and Characterization of Copper-based Catalysts

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Copper nitrate trihydrate (Cu(NO₃)₂·3H₂O), pyridine dicarboxylic acid, pyrazine, 4,4′-bipyridine, and morpholine were purchased from Sigma-Aldrich India and used as received. Nafion (product number: 274704), 5 wt% in lower aliphatic alcohols and water containing 15–20% water was obtained from Sigma-Aldrich. Carbon cloth (CC) was purchased from the electrode store in Tamil Nadu, India.

Muthukumar P., Arunkumar G., Pannipara M., Al-Sehemi A.G., Moon D, & Anthony S.P. (2023). Highly enhanced electrocatalytic OER activity of water-coordinated copper complexes: effect of lattice water and bridging ligand. RSC Advances, 13(18), 12065-12071.

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Functionalized Starch-Based Antimicrobial Coatings

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Commercial oxidized starch (OS) (carbonyl + carboxyl groups = 15.7 ± 1.2% w/w), and non-crystallizable sorbitol were provided by Ingredion (San Juan del Río, Qro., México). BW, stearic acid (SA), Tween 80 (T80), Span 60 (S60) and morpholine were supplied by Sigma (St. Louis, MO, USA). Lauric arginate ester (LAE) was acquired from Vedeqsa-Lamirsa (Terrassa, Barcelona, Spain) while natamycin (NAT) was purchased from EcoBio (Columbus, OH, USA).

Arredondo-Ochoa T., García-Almendárez B.E., Escamilla-García M., Martín-Belloso O., Rossi-Márquez G., Medina-Torres L, & Regalado-González C. (2017). Physicochemical and Antimicrobial Characterization of Beeswax–Starch Food-Grade Nanoemulsions Incorporating Natural Antimicrobials. International Journal of Molecular Sciences, 18(12), 2712.

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Synthesis of Chiral Organic Compounds

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l-Lactic acid (≥98%), l-mandelic acid (≥99%), allyl bromide, tert-butyldimethylsilyl chloride, trifluoroborane etherate, tetrakis(triphenylphosphine)palladium
(0), and morpholine were purchased from Sigma-Aldrich and used without
further purification. Glycolic acid (≥98%) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide
hydrochloride were purchased from Tokyo Chemical Industry and used
without purification. d-Phenyl lactic acid (≥95%)
was purchased from AK Scientific, Inc. and used without purification.
Dichloromethane was distilled over CaH₂ under N₂.

Lee J.M., Jang H., Lee S.W, & Kim K.T. (2022). Nondestructive Sequencing of Enantiopure Oligoesters by Nuclear Magnetic Resonance Spectroscopy. JACS Au, 2(9), 2108-2118.

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Synthesis and Purification of Quantum Dots

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Cadmium oxide (CdO, 99.99%), zinc oxide (ZnO, 99%), 1-octadecene (ODE, technical grade, 90%), linoleic acid (LA, technical grade 60–74%), oleylamine (OAm, technical grade, 90%), selenium (Se, 99.999%), phenyl isothiocyanate (PhNCS, 98%), morpholine (99%), chloroform-d (CDCl₃, 99.8 atom % D), and silica gel (high-purity grade, pore size 60 Å, 230–400 mesh particle size) were purchased from Sigma-Aldrich and used without further purification. Sodium hydroxide (NaOH, p.a.) and solvents were purchased from Fisher Scientific and used for the purification of organic precursors and QDs. Triethylamine (Et₃N, p.a.) and tetrahydrofuran (THF, p.a.) were purified by distillation over NaOH and sodium correspondingly prior to the synthesis. Syntheses of QDs were carried out using standard Schlenk techniques under an inert atmosphere.

Loghina L., Chylii M., Kaderavkova A., Slang S., Svec P., Rodriguez Pereira J., Frumarova B., Cieslar M, & Vlcek M. (2021). Highly Efficient and Controllable Methodology of the Cd0.25Zn0.75Se/ZnS Core/Shell Quantum Dots Synthesis. Nanomaterials, 11(10), 2616.

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Synthesis and Cell Proliferation Assay

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Piperazine (99.5%), lithium hydroxide (99.5%), ethylene diamine (EDA) (99.8%), cyclam (Cy) (99.5%), morpholine (99%), carbon tapes, hydrochlric acid (37 %), sodium chloride (99.5%), and tris buffer were purchased by Sigma Aldrich (Milan, Italy) and used as received. 2,2′-bisacrylamidoacetic acid (BAC) (98.4%) was obtained as previously described [17 (link)]. Cell Titer 96 Aqueous One Solution Cell Proliferation assay (MTS solution) were purchased from Promega (Milan, Italy).

Mauro N., Giammona G., Ranucci E, & Ferruti P. (2022). Synthesis of Biocompatible and Biodegradable Polyamidoamines Microgels via a Simple and Reliable Statistical Approach. Materials, 15(20), 7280.

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Synthesis and Antimicrobial Evaluation

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Starting 1H-indole-3-carboxaldehyde (purity 97%), furfural (99%), 5-methylfurfural (99%), 2-thiophenecarboxaldehyde (98%), 4-pyridinecarboxaldehyde (97%), 2-naphthaldehyde (98%), cyclohexanecarbaldehyde (97%), Lawesson’s reagent (97%), morpholine (99%), benzoyl chloride (99%), iodomethane (99%), and 2-aminobenzenesulfonamide (98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). The reagents for the analysis of the antimicrobial activity: Cefazolin—MP Biomedicals (Illkirch, France), Cefotaxime—PROMED (Saransk, Russia), Chloramphenicol—AppliChem (Darmstadt, Germany), Amikacin sulfate—Sigma-Aldrich (St. Louis, MO, USA), Fluconazole—Sigma-Aldrich (St. Louis, MO, USA), Amphotericin B—Sigma-Aldrich (St. Louis, MO, USA), Isoniazid—Sigma (St. Louis, MO, USA), LB-broth—VWR (Radnor, PA, USA), and LB-agar—Sigma (St. Louis, MO, USA).

Mendogralo E.Y., Nesterova L.Y., Nasibullina E.R., Shcherbakov R.O., Tkachenko A.G., Sidorov R.Y., Sukonnikov M.A., Skvortsov D.A, & Uchuskin M.G. (2023). The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives. Molecules, 28(14), 5348.

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Synthesis and Evaluation of Novel Compounds

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Cyclopentanone, malononitrile, morpholine,
methanesulfonic acid, acetic anhydride, DMF-DMA, acetic acid (AcOH),
hydrobromic acid (HBr), (2,5-dimethoxyphenyl)boronic acid, palladium
acetate [Pd(OAc)₂], 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl
(S-Phos), potassium phosphate (K₃PO₄), boron tribromide (BBr₃), boron trifluoride diethyl
etherate (BF₃·OEt₂), sodium borohydride
(NaBH₄), DIBAl-H, p-toluenesulfonic acid,
DPPH, ABTS, DCFH-DA, and AAPH were all purchased from Sigma-Aldrich
(St. Louis, MO, USA). Aluminum-backed 0.2 mm thick silica gel 60 F₂₅₄ plates for analytical thin-layer chromatography as well
as silica gel 60 (40–63 μm) for flash chromatographic
separations were supplied by Merck (Darmstadt, Germany). Cell culture
media were purchased from Gibco U.S. Biotechnology Co. Fetal bovine
serum (FBS) was bought from Tianhang Biotech Co. Inc. (Zhejiang, China).
5,5′,6,6′-Tetrachloro-1,1′,3,3′-tetraethyl-imidacarbocyanine
iodide (JC-1), PI, and annexin V-FITC/PI kits were obtained from Becton,
Dickinson and Company (Franklin Lakes, NJ, USA).

Chen Y, & Lan P. (2018). Total Syntheses and Biological Evaluation of the Ganoderma lucidum Alkaloids Lucidimines B and C. ACS Omega, 3(3), 3471-3481.

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