Tiquizium bromide, HSR-902, Thiaton
替喹溴铵Chemical Name: 3-(Di-2-thienylmethylene)-5-methyl-trans-quinolizidinium bromide
CAS No. 71731-58-3
项目整合开发状态: Launched-1984
项目研究机构: Abbott (Originator)
合成路线:The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III),which by treatment with SOCl2 is converted into the chloronitrile (IV).The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V),which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI).The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII),which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX).Finally,this compound is quaternirzed with methyl bromide in acetone.
📌 参考资料/链接：
参考文献标题:Substituted quinolizidine and indolizidine derivatives and the preparation thereof
文献作者:Kato,H.; Koshinaka,E.; Ogawa,N.; Kurata,S.; Yamagishi,K.; Ishikuza,M.(Hokuriku Seiyaku Co.,Ltd.)
参考来源:BE 0866988; DE 2820687; FR 2390956; GB 1602927; JP 8034148
📄 详细内容
合成路线:The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III),which by treatment with SOCl2 is converted into the chloronitrile (IV).The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V),which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI).The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII),which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX).Finally,this compound is quaternirzed with methyl bromide in acetone.
参考文献标题:Tiquizium bromide
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Thorpe,P.J.
参考来源:Drugs Fut 1982,7(9),655
合成路线:The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III),which by treatment with SOCl2 is converted into the chloronitrile (IV).The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V),which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI).The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII),which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX).Finally,this compound is quaternirzed with methyl bromide in acetone.
参考文献标题:Studies on antispasmodics.I.Synthesis and anticholinergic activity of 1-,2- and 3-diarylmethylenequinolizidine quaternary ammonium salts
文献作者:Ogawa,N.; Matsubara,I.; Kato,H.; Kurata,S.; Koshinaka,E.; Yamagishi,K.; Kubo,S.
参考来源:Chem Pharm Bull 1979,27(6),1454-63
产品链接: CAS No. 71731-58-3››