AS-2646, AD-2646
Chemical Name: 2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline dimaleate
CAS No. 94788-64-4, 72320-60-6 (diHCl), 72320-59-3 (free base)
项目整合开发状态: Phase II
项目研究机构: Dainippon Pharmaceutical (Originator)
合成路线:This compound can be prepared by two related ways:1) The reaction of 2-nitrobenzoic acid (I) with PCl5 at 50 C gives the corresponding acyl chloride (II),which by a Friedel-Craft's condensation with benzene and AlCl3 yields 2-nitrobenzophenone (III).The reduction of (III) with H2 over Pd/C in ethanol affords 2-aminobenzophenone (IV),which is acylated with acetic anhydride sodium acetate to give 2-acetamidobenzophenone (V).The cyclization of (V) by means of sodium methoxide in refluxing ethanol yields 4-phenylquinoline-2(1H)-one (VI),which by reaction with SOCl2-DMF in hot CHCl3 is converted to 2-chloro-4-phenylquinoline (VII).Finally,this compound is condensed with N-ethylpiperazine (VIII) at 130 C.2) Quinoline (VII) is condensed with piperazine (IX) as before to give 4-phenyl-2-(1-piperazinyl)quinoline (X),which is finally alkylated with ethyl iodide and sodium carbonate in refluxing butanone.
📌 参考资料/链接：
参考文献标题:2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline and its salts with acids,process for their preparation and their use as antidepressant agents
文献作者:Uno,H.; Nagai,Y.; Karasawa,T.; Furukawa,K.(Dainippon Pharmaceutical Co.,Ltd.)
参考来源:DE 2912414
📄 详细内容
合成路线:This compound can be prepared by two related ways:1) The reaction of 2-nitrobenzoic acid (I) with PCl5 at 50 C gives the corresponding acyl chloride (II),which by a Friedel-Craft's condensation with benzene and AlCl3 yields 2-nitrobenzophenone (III).The reduction of (III) with H2 over Pd/C in ethanol affords 2-aminobenzophenone (IV),which is acylated with acetic anhydride sodium acetate to give 2-acetamidobenzophenone (V).The cyclization of (V) by means of sodium methoxide in refluxing ethanol yields 4-phenylquinoline-2(1H)-one (VI),which by reaction with SOCl2-DMF in hot CHCl3 is converted to 2-chloro-4-phenylquinoline (VII).Finally,this compound is condensed with N-ethylpiperazine (VIII) at 130 C.2) Quinoline (VII) is condensed with piperazine (IX) as before to give 4-phenyl-2-(1-piperazinyl)quinoline (X),which is finally alkylated with ethyl iodide and sodium carbonate in refluxing butanone.
参考文献标题:A novel class of antiulcer agents.4-Phenyl-2-(1-piperazinyl)quinolines
文献作者:Uno,H.; Nagai,Y.; Hino,K.; Kawashima,K.; Oka,M.; Matsumoto,J.
参考来源:Chem Pharm Bull 1989,37(1),110
合成路线:This compound can be prepared by two related ways:1) The reaction of 2-nitrobenzoic acid (I) with PCl5 at 50 C gives the corresponding acyl chloride (II),which by a Friedel-Craft's condensation with benzene and AlCl3 yields 2-nitrobenzophenone (III).The reduction of (III) with H2 over Pd/C in ethanol affords 2-aminobenzophenone (IV),which is acylated with acetic anhydride sodium acetate to give 2-acetamidobenzophenone (V).The cyclization of (V) by means of sodium methoxide in refluxing ethanol yields 4-phenylquinoline-2(1H)-one (VI),which by reaction with SOCl2-DMF in hot CHCl3 is converted to 2-chloro-4-phenylquinoline (VII).Finally,this compound is condensed with N-ethylpiperazine (VIII) at 130 C.2) Quinoline (VII) is condensed with piperazine (IX) as before to give 4-phenyl-2-(1-piperazinyl)quinoline (X),which is finally alkylated with ethyl iodide and sodium carbonate in refluxing butanone.
参考文献标题:AD-2646
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1989,14(8),735
产品链接: CAS No.72320-60-6›› 产品链接: CAS No.72320-59-3››