octahydro-2H-quinolizine-3-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】32080

【品名】octahydro-2H-quinolizine-3-carbonitrile

【CA登记号】

【分子式】C₁₀H₁₆N₂

【分子量】164.25052

【元素组成】C 73.13% H 9.82% N 17.06%

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：(V)

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.

参考文献中间体

合成目标

【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