Topic
Morpholine
About: Morpholine is a research topic. Over the lifetime, 5411 publications have been published within this topic receiving 51063 citations. The topic is also known as: diethylene imidoxide & diethylene oximide.
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TL;DR: In this article, it was shown that terminal alkynes with secondary amines (dimethylamine, diethylamine and piperidine, morpholine) and CO2 in the presence of mononuclear ruthenium catalysts, afford the vinyl carbamates R1CH CHOCONR2.
59 citations
Patent•
19 Dec 1980
TL;DR: In this article, an aqueous mixture of an oxide of aluminum, a oxide of silicon, a metal or ammonium cation and a suitable oxygen-containing monomeric template compound is formed by maintaining the pH of such mixture between 9 and 14 and then crystallizing the mixture.
Abstract: Crystalline aluminosilicate molecular sieves are prepared by (1) forming an aqueous mixture of an oxide of aluminum, an oxide of silicon, a metal or ammonium cation and a suitable oxygen-containing monomeric organic template compound, (2) maintaining the pH of such mixture between 9 and 14, and (3) crystallizing the mixture The organic templates include ethanolamine, diethanolamine, triethanolamine, ethylethanolamine, ethyldiethanolamine, 2-amino-2-ethyl-1,3-propanediol, morpholine, and alkali metal complexed tetrahydrofuran, dioxane, dioxolane, and crown ethers Crystalline aluminosilicates prepared include mordenite, ferrierite, ZSM-4, and ZSM-5
59 citations
TL;DR: In this article, an experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of indole, substituted indoles, pyrazole, imidazole, benzamide, morpholine, benzimidazoles, thiobenzamide, aniline, benzylaniline.
59 citations
TL;DR: Application of the reactivity trends established for [Pd(cinnamyl)Cl](2)/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved.
Abstract: We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl](2)/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl)morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, α-branched acyclic primary alkylamines, hindered electron-rich primary anilines ≫ cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, α,α-branched primary alkylamines, and primary amides. The new isomeric ligand N-(4-(di(1-adamantyl)phosphino)phenyl)morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallographically characterized; the [Pd(cinnamyl)Cl](2)/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl](2)/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl](2)/L1 and 4-chlorotoluene (affording 5a); the alternative regioisomer (5a') was obtained when using [Pd(cinnamyl)Cl](2)/L2. These observations are in keeping with coordination chemistry studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)](+) fragment occurred via the primary amine moiety, affording the crystallographically characterized adduct [(L1)Pd(p-tolyl)(NH(2)CH(2)CH(2)(4-C(6)H(4)NH(2))](+)OTf(-) (7) in 72% yield.
58 citations
TL;DR: In this article, the termination reaction of the cationic polymerization of 2-phenyl- and 2-nonyl-2-oxazolines was examined by reacting the corresponding model oxazolinium salts having tosylate and trifluoromethansulfonate counterions with various nucleophiles.
Abstract: The termination reaction of the cationic polymerization of 2-phenyl- and 2-nonyl-2-oxazolines was examined by reacting the corresponding model oxazolinium salts having tosylate and trifluoromethansulfonate counterions with various nucleophiles. The reaction was monitored by 1 H NMR spectroscopy. Piperidine and KOH react with the oxazolinium salts very fast and quantitatively. In the case of piperidine, the use of a double molar amount of piperidine is necessary to achieve complete conversion. The addition of piperidine, pyridine, 4-dimethylaminopyridine and morpholine takes place in position 5 of the oxazolinium ring, whereas water and KOH add in position 2. The rate of the termination reaction depends on the electron density of the nucleophile which can be correlated with the pK a value. With CF 3 SO 3 - as counterion the addition of nucleophiles in position 5 is distinctly faster, whereas the addition of water in position 2 is much slower than with TsO - as counterion. The ring-opening of the nonyl oxazolinium ion is slower than that of the phenyl oxazolinium ion.
58 citations