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Sercloremine hydrochloride, CGP-4718A,54403-20-2, 54403-19-9

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摘 要:Sercloremine hydrochloride, CGP-4718A,54403-20-2, 54403-19-9 (free base),C14-H16-Cl-N-O.Cl-H,4,5-(Chloro-2-benzofuranyl)-1-methylpiperidine hydrochloride; 5-Chloro-2-(1-methyl-4-piperidyl)benzofuran hydrochloride
  • 【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〗Castaer, J.; Serradell, M.N.
  • 〖参考〗Castaer, 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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