Tefluxitol, Lu-10-022
秦氟替索Chemical Name: 2-[4-[3-[7-Fluoro-2-(trifluoromethyl)-10H-dibenzo[b,e]thiopyran-10-yl]propyl]piperazin-1-yl]ethanol
CAS No. 55837-23-5, 53542-42-0 (diHCl)
项目整合开发状态: Not Determined
项目研究机构:
合成路线:The condensation of 2-chloro-5-trifluoromethylbenzonitrile (I) with 3-fluorothiophenol (II) by means of sodium ethoxide in refluxing ethanol gives 2-(3-fluorophenylthio)-5-trifluoromethylbenzoic acid (III),which is cyclized by means of H2SO4 at 65 C yielding 6-fluoro-2-trifluoromethylthioxanthone (IV).The Grignard reaction of (IV) with 3-dimethylaminopropylmagnesium chloride (V) in refluxing THF affords 6-fluoro-2-trifluoromethyl-9-(3-dimethylaminopropyl)thioxanthene (VII).The condensation of (VII) with N-(2-hydroxyethyl)piperazine (VIII) in isopropanol at 140 C yields 6-fluoro-2-trifluoro-9-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propylidene]thioxanthene (IX),which is finally reduced with aqueous HI and red P in refluxing acetic acid.
📌 参考资料/链接：
参考文献标题:
文献作者:Buus,J.M.L.; Lassen,N.; Bigler,A.J.
参考来源:AT 332395; AT 345826; BE 845057; CA 1010870; DE 2359359; FR 2209573; FR 2320740; GB 1453828; GB 1498394; JP 7494691; JP 7739682; NL 7316035; NL 7608822; US 4042695; US 4044024; ZA 7308990; ZA 7604544
📄 详细内容
合成路线:The condensation of 2-chloro-5-trifluoromethylbenzonitrile (I) with 3-fluorothiophenol (II) by means of sodium ethoxide in refluxing ethanol gives 2-(3-fluorophenylthio)-5-trifluoromethylbenzoic acid (III),which is cyclized by means of H2SO4 at 65 C yielding 6-fluoro-2-trifluoromethylthioxanthone (IV).The Grignard reaction of (IV) with 3-dimethylaminopropylmagnesium chloride (V) in refluxing THF affords 6-fluoro-2-trifluoromethyl-9-(3-dimethylaminopropyl)thioxanthene (VII).The condensation of (VII) with N-(2-hydroxyethyl)piperazine (VIII) in isopropanol at 140 C yields 6-fluoro-2-trifluoro-9-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propylidene]thioxanthene (IX),which is finally reduced with aqueous HI and red P in refluxing acetic acid.
参考文献标题:Teflutixol
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Owen,R.T.
参考来源:Drugs Fut 1982,7(6),410
产品链接: CAS No. 55837-23-5›› 产品链接: CAS No.53542-42-0››