438056-69-0Relevant articles and documents
Microwave assisted synthesis of novel six-membered 4-C, 4-O and 4-S lactams derivatives: Characterization and in vitro biological evaluation of cytotoxicity and anticoagulant activity
Nú?ez-Navarro, Nicolás E.,Segovia, Gerardine F.,Burgos, Renato A.,Lagos, Carlos F.,Fuentes-Ibacache, Nataly,Faúndez, Mario A.,Zacconi, Flavia C.
, p. 203 - 207 (2017)
A series of six-membered lactam derivatives containing C, O and S atoms in position 4 were synthesized using microwave methodology through coupling reactions. The novel compounds were synthesized following two step reaction to yield fifteen derivatives. The final derivative N-(4-(3-oxotiomorpholin)phenyl) hexanamide was selectively toxic to the HCT-116 cell line over the HeLa cancerous and HEK-293 human non-malignant control cells with low inhibition Factor Xa (FXa) activity. The new products were characterized by spectral data including 1H and 13C nuclear magnetic resonance (NMR), infrared (IR) and high-resolution mass spectrometry (HRMS). Cytotoxicity of products on HCT-116, HeLa, HEK-293 cell lines and FXa activity assays are also reported.
Synthesis method of 4-(4-aminophenyl)-3-morpholone
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Paragraph 0053-0055, (2021/06/12)
The invention provides a synthesis method of 4-(4-aminophenyl)-3-morpholone. The method comprises the following steps: condensing p-halonitrobenzene and morpholine which are used as starting materials to generate 4-(4-nitrophenyl) morpholine, oxidizing 4-(4-nitrophenyl) morpholine by taking a halite or chlorine dioxide as an oxidizing agent and controlling the pH value of a reaction system to be less than 7 to generate 4-(4-nitrophenyl)-3-morpholone, and finally reducing to generate the target product 4-(4-aminophenyl)-3-morpholone. The synthesis method of 4-(4-aminophenyl)-3-morpholinone provided by the invention has the advantages of greenness, high efficiency, easiness in industrial application and the like.
Catalytic production of anilines by nitro-compounds hydrogenation over highly recyclable platinum nanoparticles supported on halloysite nanotubes
Aepuru, Radhamanohar,Bustamante, Tatiana M.,Campos, Cristian H.,Leal-Villarroel, Edgardo,Mangalaraja, Ramalinga Viswanathan,Shanmugaraj, Krishnamoorthy,Torres, Cecilia C.,Vinoth, Victor
, (2021/07/28)
Pt-nanoparticles supported on halloysite-nanotubes (HNTs) were selectively deposited onto the inner (Pt(IN)/HNT) or outer (Pt(OUT)/HNT) surface of the support to evaluate their operational stability on the cleaner and efficient hydrogenation of nitro compounds to produce their corresponding anilines. The formation of Pt0-aggregates on the inner or outer surfaces was observed, with mean particles sizes of 2.4–2.9 nm. The catalysts were evaluated using ethanol as solvent and nitrobenzene as a model substrate at a temperature of 298 K, under 1 bar of H2 pressure. The Pt(IN)/HNT catalyst showed better catalytic performance than Pt(OUT)/HNT, which was mainly attributed to the confinement effect of the Pt-nanoparticles inside the HNTs. However, the operational stability showed that Pt(OUT)/HNT retained its catalytic performance after 15 cycles, while the Pt(IN)/HNT catalyst suffered deactivation after the 5th cycle. The best catalytic system showed a moderate-to-high efficiency in the efficient hydrogenation of 7 nitro compounds used to produce their corresponding anilines, which are important pharmaceutical building blocks.
Gold nanoparticles supported on mesostructured oxides for the enhanced catalytic reduction of 4-nitrophenol in water
Bustamante, Tatiana M.,Campos, Cristian H.,Shanmugaraj, Krishnamoorthy,Torres, Cecilia C.
, (2020/06/21)
In this work, Au nanoparticles supported on aluminum oxide (Au/ANT) and titanate (Au/TNT) nanotubes were synthesized for their use as catalysts in the reduction of 4-nitrophenol to produce 4-aminophenol with NaBH4 as the reducing agent. The catalysts were prepared with a 0.5 % metal loading employing the nanotube supports modified with 3-aminopropyl-trimethoxysilane (APTMS) to provide plentiful anchoring sites to trap the Au nanoparticles and prevent their agglomeration. All materials were characterized using a range of analytical techniques, and it was found that Au zero-valent nanoparticles were homogenously supported on the inner/outer surfaces of the nanotubular-structured carriers. Both catalytic systems were highly active and selective in the reduction of 4-nitrophenol, giving TOF values of 20,561 and 19,560 h?1 for Au/TNT and Au/ANT, respectively. The excellent catalytic activity was attributed to the highly dispersed Au clusters on the support surfaces through enhanced functionalization with APTMS, and the confinement effect of the nanotubular carriers. Furthermore, Au/TNT exhibited a high operational stability for the reduction of 4-nitrophenol reaching 10 catalytic cycles with only a moderate decrease in the conversion level after the seventh cycle, which was attributed to a degree of metal leaching. Finally, the catalytic reduction performance of the Au/TNT catalyst was tested in different nitroarene-substituted pharmaceuticals, and revealed a high activity (>99 % after 60 min of reaction) and selectivity toward production of the desired substituted anilines, thereby highlighting the potential of this catalyst for application in these processes.
Facile preparation of 4-(4-nitrophenyl)morpholin-3-one via the acid-catalyzed selective oxidation of 4-(4-nitrophenyl)morpholine by sodium chlorite as the sole oxidant
Chu, Changhu,Jia, Qiang,Liu, Chaoyang,Qin, Cheng,Sun, Haozhou,Yang, Tiannuo,Yu, Tao
, p. 2633 - 2638 (2020/12/29)
4-(4-Nitrophenyl)morpholin-3-one and 4-(4-aminophenyl) morpholin-3-one are the key intermediates for rivaroxaban synthesis. A facile and economically efficient process has been developed for the preparation of these intermediates. Excellent yield of 4-(4-nitrophenyl)morpholine is obtained by condensing 4-chloro nitrobenzene and morpholine, and 4-(4- nitrophenyl)morpholine is oxidized using inexpensive sodium chlorite to achieve a good yield of the corresponding 4-(4- nitrophenyl)morpholin-3-one. Finally, the key intermediate of rivaroxaban, 4-(4-aminophenyl) morpholin-3-one, is achieved by the iron(III)-catalyzed reduction of the nitro group with aqueous hydrazine. No high-cost materials were used, and the process did not require column purification.
A high-purity 4 - (4 - aminophenyl) morpholine -3 - ketone (by machine translation)
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Paragraph 0079; 0080; 0081; 0083, (2019/03/15)
The invention relates to a low-cost, high-purity of 4 - (4 - aminophenyl) morpholine - 3 - one (II) of the preparation method. The use of hydroxy acetonitrile and 1, 2 - dihalo substituted ethane in the reaction process for preparing halogenated ethyl oxygen radical second grade nitrile IV, then with the para-nitroaniline III substituted reaction, acid lower ring becomes a 4 - (4 - nitrophenyl) morpholine - 3 - ketone V, 4 - (4 - nitrophenyl) morpholine - 3 - ketone V obtained by hydrogenating and reducing 4 - (4 - aminophenyl) morpholine - 3 - one II. The present invention the used raw materials are cheap and easily obtained, and the cost is low; the process route is simple, safety and environmental protection; the design of each step the reaction selectivity is high, high yield, high purity for the 4 - (4 - aminophenyl) morpholine - 3 - ketone preparation provides a guarantee, to industrial production of high-purity [...]. (by machine translation)
PROCESS FOR THE PREPARATION OF 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE
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Page/Page column 11, (2019/08/20)
The field of this invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of 4-(4-aminophenyl)morpholin-3-one of Formula (I), the key intermediate of rivaroxaban according to the scheme. In the process 2-(2-chloroethoxy)ethanol of Formula (XI) is oxidized to 2-(2-chloroethoxy)- acetic acid with aqueous sodium- or calcium-hypochlorite and a catalyst. The 2-(2~ chloroethoxy)acetic acid of Formula (X) is reacted with 4-nitro-aniline of Formula (VII) with phenylboronic acid catalyst. Then the 2-(2-chloroetoxy)-N-(4-nitrophenyl)acetamide of Formula (IX) is transformed to 4-(4-nitrophenyl)morpholin-3-one of Formula (IV) in a ?one- pot" procedure. The 4-(4-nitrophenyl)morpholin-3-one of Formula (IV) is hydrogenated to get 4-(4-aminophenyl)morpholin-3-one of Formula (I).
Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives
Sanghani, Yogesh J.,Koradiya, Suresh B.,Patel, Anilkumar S.
, p. 1461 - 1464 (2019/06/11)
A series of novel 4-(4-amino phenyl) morpholine-3-one substituted coumarin derivatives have been prepared by chloramine coupling reaction and were identified. The novel synthetic route involves nucleophilic substitution reaction of 4-chloro-3-nitro-2H-chromene-2- one with 4-(4-amino phenyl)morpholine-3-one. Due to the presence of nitro group in coumarin derivatives make substitution reaction easy and convenient at low temperature. Using DMF as solvent and K2CO3 as base various substituted 4-(4-((3-nitro-2-oxo-2H-chromen- 4-yl)amino)phenyl)morpholine-3-one derivatives (YS-1 to YS-10) can be obtain in good yield and high purity. Structural characterization of all synthesized compound was done by NMR, Mass and IR spectra.
METHOD FOR PRODUCTION OF 4-(4-AMINOPHENYL)-3-MORPHOLINON
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Paragraph 0071; 0072-0086, (2019/08/16)
PROBLEM TO BE SOLVED: To provide a method for producing 4-(4-aminophenyl)-3-morpholinon in an industrially advantageous manner. SOLUTION: By using a heterogeneous metal catalyst comprising nickel and/or cobalt, 4-(4-nitrophenyl)-3-morpholinon is allowed to react with hydrogen. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
Synthetic method of high-selectivity 4-(4-aminophenyl) morpholine-3-one
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Paragraph 0073-0074, (2019/04/30)
The invention relates to a synthetic method of high-selectivity 4-(4-aminophenyl) morpholine-3-one; according to the method, by condensation of p-nitrohalobenzene and 2-aminoethoxy acetate in the presence of an alkali, 2-(4-nitrophenyl) aminoethoxy acetate is obtained, by hydrogenation reduction under the action of a solvent and a hydrogenation catalyst, 2-(4-aminophenyl) aminoethoxy acetate is obtained, and the 4-(4-aminophenyl) morpholine-3-one is obtained by intramolecular dealcoholization cyclization. The reaction route disclosed by the invention is high in reaction selectivity, the reaction selectivity of each step reaches more than 99.0%, and the total yield is up to 96.0%. The raw materials are cheap and easy to obtain, the separation process is few, the process route is concise, and the method is low in wastewater quantity, high in reaction atom economy, green and environment-friendly in process.
