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【结 构 式】

【分子编号】39033

【品名】1-(2-bromo-1-butoxyethoxy)butane; 2-bromo-1-butoxyethyl butyl ether

【CA登记号】

【 分 子 式 】C10H21BrO2

【 分 子 量 】253.17954

【元素组成】C 47.44% H 8.36% Br 31.56% O 12.64%

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:(IV)

Compound can be prepared in two different ways: 1) The cyclization of 1,2-cyclohexanedione mono-p-tolylhydrazone (I) by means of formic acid in DMF gives 1,2,3,4-tetrahydro-6-methylcarbazole-1-one (II), which by condensation with chloroacetonitrile (A) by means of sodium ethoxide in dioxane is converted into 1,2,3,4-tetrahydro-6-methyl-9-cyanomethylcarbazole-1-one (III). Finally, this compound is submitted to a reductive cyclization with H2 over Raney-Ni in methanol at 30 atm. and 50 C. 2) The carbazolone (II) can also be condensed with 2-bromoacetaldehyde dibutylacetal (B) by means of sodium ethoxide to afford 1,2,3,4-tetrahydro-6-methyl-9-(beta,beta-dibutoxyethyl)carbazole-1-one (IV), which is cyclized with ammonium acetate in acetic acid yielding 1,2,5,6-tetrahydromethylpyrazino[3,2,1-j,k]-4H-carbazole (V). Finally, this compound is reduced with H2 over Pd/C.

1 Blancafort, P.; Castañer, J.; Thorpe, P.J.; Serradell, M.N.; Pirlindole. Drugs Fut 1980, 5, 1, 39.
2 Shvedov, V.I.; et al.; Synhtesis of 1,10-trimethylenepyrazino[1,2-a]indoles. Khim Farm Zh 1967, 1, 3, 25-30.
3 Mashkovskii, M.D.; et al.; New antidepressive preparation pyrozindole. Khim Farm Zh 1974, 8, 3, 60-63.
4 Mashkovskii, M.D.; et al.; GB 1340528 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 14443 2-chloroacetonitrile; chloroacetonitrile 107-14-2 C2H2ClN 详情 详情
(I) 39030 1,2-cyclohexanedione 1-[N-(4-methylphenyl)hydrazone] C13H16N2O 详情 详情
(II) 39031 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one C13H13NO 详情 详情
(III) 39032 2-(6-methyl-1-oxo-1,2,3,4-tetrahydro-9H-carbazol-9-yl)acetonitrile C15H14N2O 详情 详情
(IV) 39033 1-(2-bromo-1-butoxyethoxy)butane; 2-bromo-1-butoxyethyl butyl ether C10H21BrO2 详情 详情
(V) 39034 9-(2,2-dibutoxyethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one C23H33NO3 详情 详情
(VI) 39035 8-methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole C15H16N2 详情 详情
Extended Information