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【结 构 式】

【分子编号】32083

【品名】octahydro-2H-quinolizin-3-yl[di(2-thienyl)]methanol

【CA登记号】

【 分 子 式 】C18H23NOS2

【 分 子 量 】333.51876

【元素组成】C 64.82% H 6.95% N 4.2% O 4.8% S 19.23%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

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.

1 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, 6, 1454-63.
2 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 .
3 Blancafort, P.; Serradell, M.N.; Castaner, J.; Thorpe, P.J.; Tiquizium bromide. Drugs Fut 1982, 7, 9, 655.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 17614 2-(2-piperidinyl)-1-ethanol; 2-Piperidineethanol 1484-84-0 C7H15NO 详情 详情
(II) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(III) 32078 3-[2-(2-hydroxyethyl)-1-piperidinyl]propanenitrile C10H18N2O 详情 详情
(IV) 32079 3-[2-(2-chloroethyl)-1-piperidinyl]propanenitrile C10H17ClN2 详情 详情
(V) 32080 octahydro-2H-quinolizine-3-carbonitrile C10H16N2 详情 详情
(VI) 32081 ethyl octahydro-2H-quinolizine-3-carboxylate C12H21NO2 详情 详情
(VII) 32082 bromo(2-thienyl)magnesium 5713-61-1 C4H3BrMgS 详情 详情
(VIII) 32083 octahydro-2H-quinolizin-3-yl[di(2-thienyl)]methanol C18H23NOS2 详情 详情
(IX) 32084 3-[di(2-thienyl)methylene]octahydro-2H-quinolizine C18H21NS2 详情 详情
Extended Information