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Doxpicodin hydrochloride(former USAN), Doxpicomine hydrochloride, LY-108380

多匹可明多匹可明Chemical Name: 1-(1,3-Dioxan-5-yl)-N,N-dimethyl-1-(3-pyridyl)methanamine hydrochloride
CAS No. 69494-04-8, 62904-73-8 (diHCl), 62904-71-6 (free base)
项目整合开发状态: Biological Testing
项目研究机构:
合成路线:The condensation of 3-pyridincarboxaldehyde (I) with diethyl malonate (II) by means of piperidine in refluxing benzene gives diethyl (3-pyridyl)methylenemalonate (III),which by reaction with dimethylamine (A) in ether is converted into diethyl alpha-dimethylamino-(3-pyridyl)methylmalonate (IV).The reduction of (IV) with LiAlH4 in THF affords 2-[alpha-dimethylamino-(3-pyridyl)methyl]-1,3-propanediol (V),which is finally cyclized with paraformaldehyde by means of boron trifluoride ethearate in acetonitrile.(1-3)
📌 参考资料/链接:
参考文献标题:Various 5-substituted and 2,5-disubstituted 1,3-dioxanes,a new class of analgesic agents
文献作者:Booher,R.N.; et al.
参考来源:J Med Chem 1977,20(7),885

📄 详细内容


合成路线:The condensation of 3-pyridincarboxaldehyde (I) with diethyl malonate (II) by means of piperidine in refluxing benzene gives diethyl (3-pyridyl)methylenemalonate (III),which by reaction with dimethylamine (A) in ether is converted into diethyl alpha-dimethylamino-(3-pyridyl)methylmalonate (IV).The reduction of (IV) with LiAlH4 in THF affords 2-[alpha-dimethylamino-(3-pyridyl)methyl]-1,3-propanediol (V),which is finally cyclized with paraformaldehyde by means of boron trifluoride ethearate in acetonitrile.(1-3)

参考文献标题:Doxpicomine hydrochloride
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1981,6(9),548


合成路线:The condensation of 3-pyridincarboxaldehyde (I) with diethyl malonate (II) by means of piperidine in refluxing benzene gives diethyl (3-pyridyl)methylenemalonate (III),which by reaction with dimethylamine (A) in ether is converted into diethyl alpha-dimethylamino-(3-pyridyl)methylmalonate (IV).The reduction of (IV) with LiAlH4 in THF affords 2-[alpha-dimethylamino-(3-pyridyl)methyl]-1,3-propanediol (V),which is finally cyclized with paraformaldehyde by means of boron trifluoride ethearate in acetonitrile.(1-3)

参考文献标题:
文献作者:Booher,R.N.(Eli Lilly and Company)
参考来源:US 3962269


合成路线:The condensation of 3-pyridincarboxaldehyde (I) with diethyl malonate (II) by means of piperidine in refluxing benzene gives diethyl (3-pyridyl)methylenemalonate (III),which by reaction with dimethylamine (A) in ether is converted into diethyl alpha-dimethylamino-(3-pyridyl)methylmalonate (IV).The reduction of (IV) with LiAlH4 in THF affords 2-[alpha-dimethylamino-(3-pyridyl)methyl]-1,3-propanediol (V),which is finally cyclized with paraformaldehyde by means of boron trifluoride ethearate in acetonitrile.(1-3)
参考文献标题:
文献作者:Booher,R.N.(Eli Lilly and Company)
参考来源:US 3905987


产品链接: CAS No. 69494-04-8››

产品链接: CAS No.62904-71-6››