Sercloremine hydrochloride, CGP-4718A
Chemical Name: 4,5-(Chloro-2-benzofuranyl)-1-methylpiperidine hydrochloride; 5-Chloro-2-(1-methyl-4-piperidyl)benzofuran hydrochloride
CAS No. 54403-20-2, 54403-19-9 (free base)
项目整合开发状态: Phase II
项目研究机构: Novartis (Originator)
合成路线:The condensation of 5-chlorosalicyialdehyde (I) with 4-chloromethylpyridine (II) by means of K2CO3 / KI in hot DMF gives 5-chloro-2-[(4-pyridyl)methoxy]benzaldehyde (III),which is cyclized by heating at 300 C to afford 5-chloro-2-(4-pyridyl)benzofurane (IV).Quaternization of (IV) with methyl iodide in hot methanol yields 1-methyl-4-(5-chloro-2-benzofuranyl)pyridinium iodide (V),which is hydrogenated with NaBH4 in methanol giving 5-chloro-2-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)benzofurane (VI).Finally,this compound is hydrogenated further with H2 over PtO2 in methanol.
📌 参考资料/链接：
参考文献标题:Anti-depressant benzofuranyl piperidines
文献作者:Bernasconi,R.; Schenker,K.(Novartis Corp.)
参考来源:CH 592656; CH 605926; DE 2408476; FR 2219781; JP 49117474; JP 58004781; US 210655
📄 详细内容
合成路线:The condensation of 5-chlorosalicyialdehyde (I) with 4-chloromethylpyridine (II) by means of K2CO3 / KI in hot DMF gives 5-chloro-2-[(4-pyridyl)methoxy]benzaldehyde (III),which is cyclized by heating at 300 C to afford 5-chloro-2-(4-pyridyl)benzofurane (IV).Quaternization of (IV) with methyl iodide in hot methanol yields 1-methyl-4-(5-chloro-2-benzofuranyl)pyridinium iodide (V),which is hydrogenated with NaBH4 in methanol giving 5-chloro-2-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)benzofurane (VI).Finally,this compound is hydrogenated further with H2 over PtO2 in methanol.
参考文献标题:Sercloremine Hydrochloride
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1986,11(2),126
产品链接: CAS No. 54403-20-2›› 产品链接: CAS No.54403-19-9››