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,C12H21NO2,211.3067,ethyl octahydro-2H-quinolizine-3-carboxy

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摘 要:,C12H21NO2,211.3067,ethyl octahydro-2H-quinolizine-3-carboxylate
  • 【化学名】ethyl octahydro-2H-quinolizine-3-carboxylate
  • 【CAS登记号】
  • 【结构式】,C12H21NO2,211.3067,ethyl octahydro-2H-quinolizine-3-carboxy--药物合成数据库
  • 【分子式】C12H21NO2
  • 【分子量】211.3067
  • 【来源】
  • 【合成情况】 
  • 〖目标产物〗Tiquizium bromide, HSR-902, Thiaton
  • 〖合成路线〗
  • 〖合成方法〗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〗Blancafort, P.; Serradell, M.N.; Castaer, J.; Thorpe, P.J.; Tiquizium bromide. Drugs Fut 1982, 7, 9, 655
  • 〖目标产物〗Tiquizium bromide, HSR-902, Thiaton
  • 〖合成路线〗
  • 〖合成方法〗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〗Ogawa, N.; Matsubara, I.; Kato, H.; Kurata, S.; Koshinaka, E.; Yamagishi, K.; Kubo, S.; Studies on antispasmodics. I. Synthesis and anticholinergic activity of 1-, 2- and 3-diarylmethylenequinolizidine quaternary ammonium salts. Chem Pharm Bull 1979, 27, pan>【CAS登记
  • 〖目标产物〗Tiquizium bromide, HSR-902, Thiaton
  • 〖合成路线〗
  • 〖合成方法〗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〗Kato, H.; Koshinaka, E.; Ogawa, N.; Kurata, S.; Yamagishi, K.; Ishikuza, M. (Hokuriku Seiyaku Co., Ltd.); Substituted quinolizidine and indolizidine derivatives and the preparation thereof. BE 0866988; DE 2820687; FR 2390956; GB 1602927; JP 8034148
 
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