Neramexane hydrochloride, MRZ-2/279, MRZ-2/579
1,3,3,5,5-五甲基环己-1-胺盐酸盐Chemical Name: 1,3,3,5,5-Pentamethylcyclohexylamine hydrochloride
CAS No. 209185-99-9
项目整合开发状态: Phase III
项目研究机构: Merz (Originator), Forest (Licensee)
合成路线:Addition of methylmagnesium iodide to 3,3,5,5-tetramethylcyclohexanone (I) produced the tertiary alcohol (II).Subsequent treatment of alcohol (II) with hydrazoic acid in the presence of TiCl4 gave azide (III).This was then reduced with LiAlH4 to the corresponding amine,which was isolated as the hydrochloride salt.
📌 参考资料/链接：
参考文献标题:1-Amino-alkylcyclohexane NMDA receptor antagonists
文献作者:Kalvinsh,I.; Gold,M.; Parsons,C.G.R.; Jirgensons,A.; Klauss,V.(Merz Pharmaceuticals GmbH)
参考来源:JP 2002511873; WO 9901416
📄 详细内容
合成路线:In an alternative method,the Ritter reaction of alcohol (II) with chloroacetonitrile in the presence of H2SO4 yielded the chloroacetamide (IV).This was then hydrolyzed to the desired amine by treatment with thiourea in HOAc-EtOH.
参考文献标题:A practical synthesis of tert-alkylamines via the Ritter reaction with chloroacetonitrile
文献作者:Jirgensons,A.; et al.
参考来源:Synthesis (Stuttgart) 2000,(12),1709
合成路线:Addition of methylmagnesium iodide to 3,3,5,5-tetramethylcyclohexanone (I) produced the tertiary alcohol (II).Subsequent treatment of alcohol (II) with hydrazoic acid in the presence of TiCl4 gave azide (III).This was then reduced with LiAlH4 to the corresponding amine,which was isolated as the hydrochloride salt.
参考文献标题:Synthesis and structure-affinity relationships of 1,3,5-alkylsubstituted cyclohexylamines binding at NMDA receptor PCP site
文献作者:Jirgensons,A.; Kauss,V.; Kalvinsh,I.Ya.; Gold,M.R.; Danysz,W.; Parsons,C.G.; Quack,G.
参考来源:Eur J Med Chem 2000,35(6),555
产品链接: CAS No. 209185-99-9››