446292-04-2Relevant articles and documents
Synthesis, Characterization, and Biological Evolution of New Pyrazole Derivatives of 4-(4-Aminophenyl)morpholin-3-one through Ugi Reaction
Joshi, Harsh H.,Parsania, M. V.
, p. 247 - 253 (2021/08/03)
A new heterocyclic library was synthesized using multicomponent reactions (MCRs). A green strategy during which a set of molecules with an excellent diversity is generated with a minimum of synthetic effort, time, and by-products formation. This new series prepared using the Ugi MCRs in which aldehyde, amine, acid, and isocyanide reacts to make α-bisamide. During this work, we practice the Ugi reaction to synthesize an extremely functionalized heterocyclic library which was characterized and tested for biological evaluation. This innovative synthetic route involves for pyrazole derivatives of 4-(4-aminophenyl)morpholin-3-one by Ugi four component reaction and methanol as a solvent in good yield and high purity. All the produced compounds of library were characterized using 1H-NMR, IR, and mass spectroscopic methods.
Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
supporting information, (2020/12/21)
A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
Synthesis method of 4-(4-aminophenyl)-3-morpholone
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, (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.
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.
PROCESS FOR THE PREPARATION OF 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE
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Page/Page column 10, (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).
A high-purity 4 - (4 - aminophenyl) morpholine -3 - ketone (by machine translation)
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Paragraph 0077; 0078, (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)
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.
Preparation method of 4-(4-aminophenyl)-3-molindone
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Paragraph 0067; 0071, (2018/11/03)
The invention provides a preparation method of 4-(4-aminophenyl)-3-molindone. The preparation method has the advantages that reaction steps with high risk and high environmental pressure are omitted,especially the use of mixed acid and chloroacetyl chloride is avoid, so that the pressure of environmental protection is reduced; in addition, the use of strong oxidants such as potassium permanganateis avoided, so that the production of by-products is reduced, the synthesis yield is high, the product quality is good and the purification of reaction post treatment is facilitated; besides, all thesteps related in the reaction process are easy to carry out, so that the reaction in which passivation effect of functional groups and the like are difficult to generate in an existing method is avoided, for example, the route which takes p-nitroaniline as a raw material to carry out substitution reaction is almost impossible to perform; besides, the selected raw materials such as p-fluoronitrobenzene and bromoethylamine hydrobromide, disclosed by the invention are easy to obtain; compared with the molindone and other raw materials involved in the existing method, the preparation method is low in price and is suitable for industrialized production.
The preparation method of the [...] (by machine translation)
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, (2018/11/22)
The invention provides a method for preparing [...], using 4 - (4 - aminophenyl) - 3 - morpholone and 5 - chloro - N - (2 - ethylene oxide-based methyl) - 2 - thiophene carboxamide reaction to obtain 5 - [...] - 2 - {(R)- 2 - hydroxy - 3 - [4 - (3 - oxo - 4 - morpholinyl) phenyl amino] - propyl} amide, then adding N, N' - carbonyl di-imidazole, 4 - dimethylamino pyridine, begins to stir, heating reaction to obtain the - 5 - chloro - N - (( (5 S) - 2 - oxo - 3 - (4 - (3 - oxo-morpholine - 4 - yl) phenyl) - 1, 3 - Oxacillin - 5 - yl) methyl) thiophene - 2 - carboxamide. The technique of the invention route after the condition is optimized, mild reaction, high yield. (by machine translation)
A the advantage cuts down Sha Ban preparation method of the midbody and intermediate
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Paragraph 0238; 0242; 0243; 0244, (2017/08/25)
The invention discloses a preparation method of a rivaroxaban intermediate and an intermediate. The invention discloses a preparation method of a compound represented by the formula 4. The preparation method comprises a step of making a compound 3 carry out a ring closing reaction, which is represented in the description, so as to obtain the compound 4. The invention also discloses a preparation method of a compound represented by the formula 3 and a preparation method of a compound represented by the formula 1. The invention also discloses a compound represented by the formula 3 and a compound represented by the formula 5. The preparation method has the advantages of easily-available and cheap raw materials, simple technology and post-treatment, easy purification of intermediate and end products, high total yield, and high purity, and is easy for being applied to industrial production.
