Secoverine
司考维林Chemical Name: 1-Cyclohexyl-4-[ethyl(p-methoxy-alpha-methylphenethyl)amino]-1-butanone
CAS No. 57558-44-8, 57558-46-0 (HCl)
项目整合开发状态: Biological Testing
项目研究机构: Roche Bioscience (Originator)
合成路线:This compound can be obtained in three different ways:1) The condensation of N-ethyl-N-(p-methoxy-alpha-methylphenylethyl)amine (I) with 2-cyclohexyl-2-(3-chloropropyl)-1,3-dioxolane (II) by means of NaI in refluxing butanone gives 2-[3-(N-ethyl)-N-(p-methoxy-alpha-methylphenylethyl)amino]propyl-2-cyclohexyl-1,3-dioxolane (III),which is hydrolyzed with H2SO4 in refluxing acetone.2) By the Grignard reaction of cyclohexylmagnesium bromide (V) with 4-[N-ethyl-N-(p-methoxy-alpha-methylphenylethyl)amino]butyric acid ethyl ester (IV) in ether.3) By condensation of 2-[N-ethyl-N-(p-methoxy-alpha-methylphenylethyl)amino]ethyl chloride (VI) with cyclohexoylacetic acid ethyl ester (VII) by means of sodium in hot toluene.
📌 参考资料/链接：
参考文献标题:Secoverine hydrochloride
文献作者:Serradell,M.N.; Thorpe,P.J.; Blancafort,P.; Castar,J.
参考来源:Drugs Fut 1981,6(4),239
📄 详细内容
合成路线:This compound can be obtained in three different ways:1) The condensation of N-ethyl-N-(p-methoxy-alpha-methylphenylethyl)amine (I) with 2-cyclohexyl-2-(3-chloropropyl)-1,3-dioxolane (II) by means of NaI in refluxing butanone gives 2-[3-(N-ethyl)-N-(p-methoxy-alpha-methylphenylethyl)amino]propyl-2-cyclohexyl-1,3-dioxolane (III),which is hydrolyzed with H2SO4 in refluxing acetone.2) By the Grignard reaction of cyclohexylmagnesium bromide (V) with 4-[N-ethyl-N-(p-methoxy-alpha-methylphenylethyl)amino]butyric acid ethyl ester (IV) in ether.3) By condensation of 2-[N-ethyl-N-(p-methoxy-alpha-methylphenylethyl)amino]ethyl chloride (VI) with cyclohexoylacetic acid ethyl ester (VII) by means of sodium in hot toluene.
参考文献标题:
文献作者:Hartog,J.; Zwagemakers,J.M.A.
参考来源:US 3996245
产品链接: CAS No. 57558-44-8›› 产品链接: CAS No.57558-46-0››