Pravadoline, Win-48098-6(maleate), Win-48098
普拉朵林Chemical Name: 2-Methyl-3-(4-methoxybenzoyl)-1-[2-(4-morpholinyl)ethyl]-1H-indole; p-Methoxyphenyl 2-methyl-1-(2-morpholinoethyl)indol-3-yl ketone
CAS No. 92623-83-1, 92623-84-2 (maleate)
项目整合开发状态: Phase II
项目研究机构: Sanofi-Aventis (Originator)
合成路线:This compound can be obtained by two related ways:1) The condensation of 2-methylindole (I) with 2-morpholinoethyl chloride (II) by means of KOH in hot DMSO gives 1-(2-morpholinoethyl)-2-methylindole (III),which is then submitted to a Friedel-Craft's reaction with 4-methoxybenzoyl chloride (IV) by means of AlCl3 in dichloromethane or ethylene dichloride.2) The condensation of indole (I) with acyl chloride (IV) by means of methylmagnesium bromide in anhydrous ethyl ether gives 2-methyl-3-(4-methoxy benzoyl)indole (V),which is then condensed with morpholine (II) by means of K2CO3 in DMF.
📌 参考资料/链接：
参考文献标题:3-Carbonyl-1-aminoalkyl-1H-indoles useful as analgesics and preparation thereof
文献作者:Bell,M.R.(Sanofi-Synthabo)
参考来源:AU 8545764; EP 0171037; ES 8609246; ES 8800149; ES 8800901; ES 8800902; ES 8801203; JP 1986047463
📄 详细内容
合成路线:This compound can be obtained by two related ways:1) The condensation of 2-methylindole (I) with 2-morpholinoethyl chloride (II) by means of KOH in hot DMSO gives 1-(2-morpholinoethyl)-2-methylindole (III),which is then submitted to a Friedel-Craft's reaction with 4-methoxybenzoyl chloride (IV) by means of AlCl3 in dichloromethane or ethylene dichloride.2) The condensation of indole (I) with acyl chloride (IV) by means of methylmagnesium bromide in anhydrous ethyl ether gives 2-methyl-3-(4-methoxy benzoyl)indole (V),which is then condensed with morpholine (II) by means of K2CO3 in DMF.
参考文献标题:WIN-48098
文献作者:Castar,R.M.; Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1987,12(9),867
产品链接: CAS No. 92623-83-1›› 产品链接: CAS No.92623-84-2››