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【结 构 式】

【分子编号】49455

【品名】7,9-Dioxo-8-azaspiro[4.5]decane-6,10-dicarbonitrile

【CA登记号】

【 分 子 式 】C11H11N3O2

【 分 子 量 】217.22736

【元素组成】C 60.82% H 5.1% N 19.34% O 14.73%

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:(III)

Treatment of ethyl cyanoacetate derivative (I) with cyanoacetamide (II) in EtOH in the presence of NaOEt provides dicyano derivative (III), which is then converted into diimide (IV) by treatment with refluxing sulfuric acid. Alternatively, (IV) can also be obtained by reaction between cyclopentanone (V), cyanoacetamide (II) and piperidine by means of KOH or NaOH in H2O (or H2O/EtOH) to provide mononitrile derivative (VI), which is then refluxed with H2SO4. Double N-alkylation of compound (IV) with chloride (VII) by heating with NaH or alkaline carbonate in DMF yields dialkylated compound (VIII), which is reduced with LiAlH4 or Red-Al in refluxing THF/toluene to furnish the free base (IX). Finally, (IX) is converted into the desired dihydrochloride by treatment with HCl in isopropanol.

1 McElvain, S.M.; Clemens, D.H.; Piperidine derivatives. XXX. 1,4-Dialkyl-4-arylpiperidines. J Am Chem Soc 1958, 80, 3915.
2 Thole, F.B.; Thorpe, J.F.; The formation and reactions of imino-compounds. Part XV. The production of imino-derivatives of piperidine leading to the formation of the betabeta-disubstituted glutaric acids. J Chem Soc 1911, 99, 422.
3 Schon, U.; et al.; Synthesis, pharmacological characterization, and quantitative structure-activity relationship analyses of 3,7,9,9-tetraalkylbispidines: Derivatives with specific bradycardic activity. J Med Chem 1998, 41, 3, 318.
4 Shon, U.; Hachmeister, B.; Kehrbach, W.; Kuhl, U.; Buschmann, G. (Kali-Chemie AG); New 3,7-diazabicylo[3.3.1]nonanes. DE 3234697; EP 0103833; JP 1993247039 .
5 Schon, U.; Heitmann, W.; Matzel, U. (Kali-Chemie AG); Medicament containing crystalline fumaric acid salts or 9,9-alkylen-3-7-diazabicyclononane cpds.. DE 4139763; EP 0550383; JP 1993247040 .
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) 43191 ethyl 2-cyano-2-cyclopentylideneacetate 5407-83-0 C10H13NO2 详情 详情
(II) 12122 Cyanoacetamide; 2-Cyanoacetamide 107-91-5 C3H4N2O 详情 详情
(III) 49455 7,9-Dioxo-8-azaspiro[4.5]decane-6,10-dicarbonitrile C11H11N3O2 详情 详情
(IV) 49456   C11H12N2O4 详情 详情
(V) 15113 cyclopentanone 120-92-3 C5H8O 详情 详情
(VI) 49457 10-cyano-7-imino-9-oxo-8-azaspiro[4.5]decane-6-carboxamide C11H14N4O2 详情 详情
(VII) 29776 1-(chloromethyl)cyclopropane 5911-08-0 C4H7Cl 详情 详情
(VIII) 49458   C19H24N2O4 详情 详情
(IX) 49459   C19H32N2 详情 详情
Extended Information