- Synthetic method of flibaserin
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The invention relates to a synthesis method of flibaserin, and belongs to the technical field of organic synthesis. The method comprises the following steps: by taking methyl anthranilate as an initial raw material, firstly carrying out amido alkylation reaction on the methyl anthranilate and 1-(2-chloroethyl)-4-[3-(trifluoromethyl) phenyl] piperazine dihydrochloride under the action of alkali, then, carrying out alkaline hydrolysis to remove methyl ester, and finally, carrying out schmidt reaction under the action of diphenylphosphoryl azide to obtain the flibaserin. The method is novel in route design, short in synthesis step and few in by-products; and the method has the advantages of simple operation, simple post-treatment process, low requirements on reaction equipment, cheap and easily available raw materials, economy, environmental protection and suitableness for industrial production.
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Paragraph 0038-0039; 0041; 0043-0044; 0046-0047; 0049-0050
(2021/09/21)
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- Preparation method of Flibanserin intermediate
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The invention discloses a preparation method of a Flibanserin intermediate. The preparation method comprises: preparing 2-(4-(3-trifluoromethylphenyl)piperazine-1-ethanol from a hydrochloride of 1-(3-trifluoromethyl-phenyl)piperazine and 2-haloethanol or
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- A new method for synthesizing flibanserin (by machine translation)
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The invention relates to a new method for synthesizing of flibanserin, which belongs to the technical field of organic synthesis. The invention respectively in order to triethanolamine and between amino benzotrifluoride as the starting material, to prepare the piperazine intermediate; then to the O-phenylene diamine and the original four carbonate as raw material, the preparation of the ethoxy and imidazole intermediate; the obtained piperazine intermediate and benzimidazole intermediate undergo the substitution reaction, and hydrochloric acid deprotection to obtain the target product of flibanserin. The invention has few synthetic steps, few by-products, intermediate products and the target product yield is relatively high, intermediate product 2 - ethoxy and imidazole yield up 94.2%, the target product yield can reach 56.2%, it can be seen, the invention overcomes the substance in the prior art synthesis step is tedious, and more byproducts, target low yield of product defect. In addition, the present invention has a simple structure, high purity of product, the economic and environmental protection industrial line, has a very wide range of use and potential economic benefits. (by machine translation)
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Paragraph 0052; 0062; 0069; 0070; 0078; 0079; 0080; 0081
(2019/02/04)
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- N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines
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Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.
- Bugaenko, Dmitry I.,Yurovskaya, Marina A.,Karchava, Alexander V.
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p. 6389 - 6393
(2018/10/09)
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- Preparation method of flibaserin
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The invention relates to a preparation method of flibaserin. The method comprises the specific steps of taking o-phenylenediamine, ethyl acetoacetate, 1, 2-dibromoethane, piperazine and bromobenzotrifluoride as materials, and performing ring closing reaction, amination reaction, amination reaction, deprotection reaction and coupling reaction on the materials, so as to form flibaserin. The preparation method is high in yield, low in cost, easy to operate and suitable for industrialization.
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- Method for industrial-scale efficient preparation of high-quality Flibaserin
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The invention discloses a method for industrial-scale efficient preparation of high-quality Flibaserin, and belongs to the technical field of drug synthesis. The method comprises the following steps: A, putting benzimidazolone shown in Formula I and dihal
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Paragraph 0144; 0148
(2017/10/22)
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- A new process for preparing flibanserin (by machine translation)
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The invention discloses a new process for preparing of flibanserin. In order to 1 - isopropenyl - 2 - benzimidazolone as raw materials, first with 2 - bromo ethanol reaction, to produce intermediate 1, intermediate 1 generated by the reaction with a sulfo
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- A new process for preparing flibanserin (by machine translation)
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The invention discloses a new process for preparing of flibanserin. The craft in order to 1 - benzyl or substituted benzyl - 2 - benzimidazolone as raw materials, first with 1, 2 - Dibromoethane reaction, to produce intermediate 1, intermediate 1 with 1 - (3 - trifluoromethylphenyl) piperazine salt to produce intermediate 2, intermediate 2 in presence of catalyst hydrogenation to remove the protecting group to obtain the flibanserin, the method cheap, simple operation method, mild reaction conditions, with potential industrial value. Wherein R1 , R2 , R3 , R4 , R5 The following substituent selected from the group H, CH3 , Cl, Br, OCH3 . (by machine translation)
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- The preparation method of the flibanserin
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The invention discloses a preparation method of flibanserin. The preparation method uses trifluoromethylbenzene, triamine (2-halogen ethyl) and ortho-nitroaniline which are easy to obtain as raw materials and adopts classical elementary reactions such as cyclization, substitution, reduction and condensation, so that the flibanserin is prepared. The raw materials of the preparation method are easy to obtain, the technology is succinct, the yield is high, the preparation method is economical and environment-friendly, and a new preparation way is provided for the industrial production of the flibanserin.
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- Preparation method of flibaserin intermediate
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The invention discloses a method belonging to the field of heterocyclic compounds, and concretely relates to a preparation method of a flibaserin intermediate. The preparation method comprises the following steps of (1) dissolving 1-(3-trifluoromethylphenyl) piperazine hydrochloride in a solvent a, and reacting with 2-halogenated ethanol or ethylene oxide in the presence of alkali to obtain 2-(4-(3-trifluoromethylphenyl) piperazine-1-ethanol; (2) reacting the 2-(4-(3-trifluoromethylphenyl) piperazine-1-ethanol with a chloride agent compound to obtain a compound as shown in a formula I. According to the preparation method, the reaction selectivity is improved, the generation of impurities is reduced, the product purity is improved, and the preparation method is simple and convenient to operate, environmentally-friendly, and beneficial for industrialized mass production.
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Paragraph 0045; 0046; 0047; 0048; 0049
(2017/07/19)
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- A preparation method of flibanserin (by machine translation)
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The invention discloses a method for preparing of flibanserin, includes the steps of: (1) compound I with dichloroethane reaction to obtain compound II, its without purification, directly with compound III reaction, to obtain the compound IV; (2) compound
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- A Facile Route of Synthesis for Making Flibanserin
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A novel and efficient route of synthesis for making flibanserin via 2-ethoxy-1H-benzo[d]imidazole (12) was described with excellent yield. This protocol provided a more facile approach to flibanserin.
- Yang, Feipu,Wu, Chunhui,Li, Zhiqiang,Tian, Guanghui,Wu, Jianzhong,Zhu, Fuqiang,Zhang, Jian,He, Yang,Shen, Jingshan
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p. 1576 - 1580
(2016/09/23)
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- PROCESS FOR THE PREPARATION OF FLIBANSERIN INVOLVING NOVEL INTERMEDIATES
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The present invention related to process for the preparation of flibanserin involving novel intermediates. 1,3-dihydro-1-(2-bromoethyl)- 3-isopropenyl-2H-benzimidazol-2-one reacts with diethanolamine and converting the obtained dihydroxy compound to 1,3-dihydro- 1-[2-[N-[bis-(2-chloroethyl)amino]ethyl]-3-isopropenyl-2H-benzimidazol-2-one followed by depotection to obtain 1,3-dihydro- 1-[2-[N-bis-(2-chloroethyl)amino]ethyl]-1,2-H-benzimidazol-2-one. This on condensing with m-trifluoromethyl aniline gives flibanserin hydrochloride.
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Page/Page column 18
(2010/11/18)
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- BENZIMIDAZOLONE DERIVATIVES
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Pharmacologically active benzimidazolone derivatives as 5-HT. sub.1A and 5-HT 2 receptors, useful in the treatment of CNS disorders, of formula: STR1 wherein the substituents are defined herein.
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- Benzimidazolone derivatives as 5-HT1A and 5-HT2 antagonists
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Pharmacologically active benzimidazolone derivatives as 5-HT1Aand 5-HT2 receptors, useful in the treatment of CNS disorders of formula: wherein, R1 and R2 may be at the same time or not a hydrogen atom, halogen, trifluoromethyl, C1 6 alkyl, C1 6 alkoxy, C1 6 alkylthio, C1 6 acyl, carboxyl, C1 6 alkoxy- carbonyl, hydroxy, nitro, amino optionally C1 4 alkyl N-mono or di-substituted, C1 6 acylamino, C1 6 alkoxycarbonylamino, carbamoyl optionally C1 4 alkyl N-mono or di-substituted, cyano, C1 6 alkylsulphinyl, C1 6 alkylsulphonyl, amino sulphonyl optionally C1 4 alkyl N-mono or di-substituted, C1 4 alkyl N-mono or di-substituted aminosulphonylamino, aminosulphonylamino;, R3 is hydrogen, C1 6 alkyl, C2 6 alkenyl or C2-C6 alkynyl;, A is -CO- or -CONH- or it is absent;, B is a straight or branched, saturated or unsaturated C2 6 alkyl;, m and n are both independently an integer from 1 to 3;, R4 is an aryl, aralkyl, a heteroaryl or heteroaralkyl group, each group being optionally substituted by one or more substituents selected from halogen, trifluoromethyl, cyano, C1 3 alkoxy, C1 4 alkyland acid addition salts thereof., The process for the preparation of the compounds of formula I as well as pharmaceutical compositions containing them are also described.
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