2,2,2-trichloro-1-[4-(2-methoxyphenyl)-1-piperazinyl]-1-ethanone -Drug Synthesis Database

【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 合成路线2

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.

参考文献中间体

合成目标

【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)

参考文献中间体

合成目标

【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

Extended Information