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【结 构 式】

【分子编号】34164

【品名】1-(8,9-dichloro-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)-1-ethanone

【CA登记号】

【 分 子 式 】C12H13Cl2NO

【 分 子 量 】258.14676

【元素组成】C 55.83% H 5.08% Cl 27.47% N 5.43% O 6.2%

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 condensation of 2,3-dichlorobenzaldehyde (I) with 2,2-dimethoxyethylamine (II) in refluxing toluene gives the corresponding Schiff base (III), which is reduced with H2 over PtO2 in ethyl acetate and acetylated with acetic anhydride yielding N-(2,3-dichlororobenzyl)-N-(2,2-dimethoxyethyl)acetamide (IV). The cyclization of (IV) with AlCl3 in dichloroethane affords 7,8-dichloro-2-acetyl-1,2-dihydroisoquinoline (V), which is submitted to cyclopropanation with CHCl3, NaOH and benzyltriethylammonium chloride giving 1,1,4,5-tetrachloro-2-acetyl-1a,2,3,7b-tetrahydro-1H-cycloprop[c]isoquinoline (VI). Ring opening of (VI) by refluxing with tert-butyl alcohol yields 2-acetyl-3-(tert-butoxy)-4,8,9-trichloro-2,3-dihydro-1H-2-benzazepine (VII), which is reduced with H2 over PtO2 in methanol affording 2-acetyl-8,9-dichloro 2,3,4,5-tetrahydro-1H-2-benzazepine (VIII). Finally, this compound is desacetylated by means of refluxing aqueous HCl.

1 Perchonock, C.D.; Lantos, I.; Holden, K.G.; Finkelstei, J.A.; Facile synthesis of halo-substituted tetrahydroisoquinolines and tetrahydro-2-benzazepines via N-acetyl-1,2-dihydroisoquinolines. J Org Chem 1980, 45, 10, 1950-53.
2 Serradell, M.N.; Castaner, J.; LY-134046. Drugs Fut 1984, 9, 4, 268.
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) 14742 2,3-dichlorobenzaldehyde 6334-18-5 C7H4Cl2O 详情 详情
(II) 34158 aminoacetaldehyde dimethylacetal; 2,2-dimethoxy-1-ethanamine; 2,2-dimethoxyethylamine 22483-09-6 C4H11NO2 详情 详情
(III) 34159 N-[(Z)-(2,3-dichlorophenyl)methylidene]-2,2-dimethoxy-1-ethanamine; N-[(Z)-(2,3-dichlorophenyl)methylidene]-N-(2,2-dimethoxyethyl)amine C11H13Cl2NO2 详情 详情
(IV) 34160 N-(2,3-dichlorobenzyl)-N-(2,2-dimethoxyethyl)acetamide C13H17Cl2NO3 详情 详情
(V) 34161 1-[7,8-dichloro-2(1H)-isoquinolinyl]-1-ethanone C11H9Cl2NO 详情 详情
(VI) 34162 1-(1,1,4,5-tetrachloro-1,1a,3,7b-tetrahydro-2H-cyclopropa[c]isoquinolin-2-yl)-1-ethanone C12H9Cl4NO 详情 详情
(VII) 34163 1-[3-(tert-butoxy)-4,8,9-trichloro-1,3-dihydro-2H-2-benzazepin-2-yl]-1-ethanone C16H18Cl3NO2 详情 详情
(VIII) 34164 1-(8,9-dichloro-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)-1-ethanone C12H13Cl2NO 详情 详情
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