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  • Sercloremine hydrochloride, CGP-4718A,54403-20-2, 54403-19-9--药物合成数据库
  • 发布时间:2004-10-25 来源:本站整理
  • 【药物名称】
    Sercloremine hydrochloride, CGP-4718A
    【化学名】
    4,5-(Chloro-2-benzofuranyl)-1-methylpiperidine hydrochloride; 5-Chloro-2-(1-methyl-4-piperidyl)benzofuran hydrochloride
    【CAS登记号】
    54403-20-2, 54403-19-9 (free base)
    【结构式】
    Sercloremine hydrochloride, CGP-4718A,54403-20-2, 54403-19-9--药物合成数据库
    【分子式】
    C14-H16-Cl-N-O.Cl-H
    【分子量】
    286.2003
    【原研厂家】
    Novartis (Originator)
    【作用类别】
    Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS
    【研发状态】
    Phase II
    【合成情况】
     
    〖来源〗
    Drugs Fut
    〖合成路线〗
    〖标题〗
    Sercloremine Hydrochloride
    〖合成方法〗
    The condensation of 5-chlorosalicyialdehyde (I) with 4-chloromethylpyridine (II) by means of K2CO3 / KI in hot DMF gives 5-chloro-2-[(4-pyridyl)methoxy]benzaldehyde (III), which is cyclized by heating at 300 C to afford 5-chloro-2-(4-pyridyl)benzofurane (IV). Quaternization of (IV) with methyl iodide in hot methanol yields 1-methyl-4-(5-chloro-2-benzofuranyl)pyridinium iodide (V), which is hydrogenated with NaBH4 in methanol giving 5-chloro-2-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)benzofurane (VI). Finally, this compound is hydrogenated further with H2 over PtO2 in methanol.
    〖作者〗
    Casta馿r, J.; Serradell, M.N.
    〖参考〗
    Casta馿r, J.; Serradell, M.N.; Sercloremine Hydrochloride. Drugs Fut 1986, 11, 2, 126
    〖出处〗
    Drugs Fut1986,11,(2):126
    〖备注〗
    Synthesis of 090010: The condensation of 5-chlorosalicyialdehyde (I) with 4-chloromethylpyridine (II) by means of K2CO3 / KI in hot DMF gives 5-chloro-2-[(4-pyridyl)methoxy] benzaldehyde (III), which is cyclized by heating at 300?to afford 5-chloro-2-(4-pyridyl)benzofurane (IV). Quaternization of (IV) with methyl iodide in hot methanol yields 1-methyl-4-(5-chloro-2-benzofuranyl)pyridinium iodide (V), which is hydrogenated with NaBH4 in methanol giving 5-chloro-2-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)benzofurane (VI). Finally this compound is hydrogenated further with H2 over PtO2 in methanol (1). (Scheme 09001001a) Description Crystals, m.p. 260? free base, m.p. 107?(1). Manufacturer Ciba-Geigy (Switzerland). Reference 1. Schenker, K. and Bernasconi, R. (Ciba-Geigy A.G.); CH 592.656, CH 605.926, DE 2.408.476.
    〖来源〗
    CH 592656; CH 605926; DE 2408476; FR 2219781; JP 49117474; JP 58004781; US 210655
    〖合成路线〗
    〖标题〗
    Anti-depressant benzofuranyl piperidines
    〖合成方法〗
    The condensation of 5-chlorosalicyialdehyde (I) with 4-chloromethylpyridine (II) by means of K2CO3 / KI in hot DMF gives 5-chloro-2-[(4-pyridyl)methoxy]benzaldehyde (III), which is cyclized by heating at 300 C to afford 5-chloro-2-(4-pyridyl)benzofurane (IV). Quaternization of (IV) with methyl iodide in hot methanol yields 1-methyl-4-(5-chloro-2-benzofuranyl)pyridinium iodide (V), which is hydrogenated with NaBH4 in methanol giving 5-chloro-2-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)benzofurane (VI). Finally, this compound is hydrogenated further with H2 over PtO2 in methanol.
    〖作者〗
    Bernasconi, R.; Schenker, K. (Novartis Corp.)
    〖参考〗
    Bernasconi, R.; Schenker, K. (Novartis Corp.); Anti-depressant benzofuranyl piperidines. CH 592656; CH 605926; DE 2408476; FR 2219781; JP 49117474; JP 58004781; US 210655
    〖出处〗
    CH 592656; CH 605926; DE 2408476; FR 2219781; JP 49117474; JP 58004781; US 210655,,():
    〖备注〗
    Synthesis of 090010: The condensation of 5-chlorosalicyialdehyde (I) with 4-chloromethylpyridine (II) by means of K2CO3 / KI in hot DMF gives 5-chloro-2-[(4-pyridyl)methoxy] benzaldehyde (III), which is cyclized by heating at 300?to afford 5-chloro-2-(4-pyridyl)benzofurane (IV). Quaternization of (IV) with methyl iodide in hot methanol yields 1-methyl-4-(5-chloro-2-benzofuranyl)pyridinium iodide (V), which is hydrogenated with NaBH4 in methanol giving 5-chloro-2-(1-methyl-1,2,3,6-tetrahydro-4-pyridyl)benzofurane (VI). Finally this compound is hydrogenated further with H2 over PtO2 in methanol (Scheme 09001001a).
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