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【结 构 式】

【分子编号】48007

【品名】2,2,2-trichloro-1-[4-(2-methoxyphenyl)-1-piperazinyl]-1-ethanone

【CA登记号】

【 分 子 式 】C13H15Cl3N2O2

【 分 子 量 】337.63248

【元素组成】C 46.25% H 4.48% Cl 31.5% N 8.3% O 9.48%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

1-(2-Methoxyphenyl)-4-trichloroacetylpiperazine (II), prepared from 1-(2-methoxyphenyl)piperazine (I) and trichloroacetyl chloride, was treated with chlorosulfonic acid to give the sulfonyl chloride (III). Coupling of chloride (III) with 2,5-dibromo-3-fluoroaniline (IV) afforded sulfonamide (IV). Finally, removal of the trichloroacetyl protecting group under basic conditions provided the title piperazine derivative.

2 Moss, S.F.; Bromidge, S.M. (SmithKline Beecham plc); Novel cpds.. WO 9902502 .
1 Bromidge, S.M.; Gager, T.; Clarke, S.E.; et al.; Phenyl benzenesulfonamides are novel and selective 5-HT6 antagonists: Identification of N-(2,5-dibromo-3-fluorophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide (SB-357134). Bioorg Med Chem Lett 2001, 11, 1, 55.
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) 11882 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine 35386-24-4 C11H16N2O 详情 详情
(II) 48007 2,2,2-trichloro-1-[4-(2-methoxyphenyl)-1-piperazinyl]-1-ethanone C13H15Cl3N2O2 详情 详情
(III) 48008 4-methoxy-3-[4-(2,2,2-trichloroacetyl)-1-piperazinyl]benzenesulfonyl chloride C13H14Cl4N2O4S 详情 详情
(IV) 48009 2,5-dibromo-3-fluoroaniline; 2,5-dibromo-3-fluorophenylamine C6H4Br2FN 详情 详情
(V) 48010 N-(2,5-dibromo-3-fluorophenyl)-4-methoxy-3-[4-(2,2,2-trichloroacetyl)-1-piperazinyl]benzenesulfonamide C19H17Br2Cl3FN3O4S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

N-(2-Methoxyphenyl)piperazine (I) is protected as the trichloroacetamide (II) using trichloroacetyl chloride and diisopropylethylamine. Then, chlorosulfonation of (II) in cold CH2Cl2 furnishes sulfonyl chloride (III)

1 Bromidge, S.M.; Moss, S.F. (GlaxoSmithKline plc); N-(3,5-Dichloro-2-methoxyphenyl)-4-methoxy-3-piperazin-1-yl-benzenesulfonamide. EP 1313720; WO 0218358 .
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) 11882 1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine 35386-24-4 C11H16N2O 详情 详情
(II) 48007 2,2,2-trichloro-1-[4-(2-methoxyphenyl)-1-piperazinyl]-1-ethanone C13H15Cl3N2O2 详情 详情
(III) 48008 4-methoxy-3-[4-(2,2,2-trichloroacetyl)-1-piperazinyl]benzenesulfonyl chloride C13H14Cl4N2O4S 详情 详情
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