2-chloro-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】30011

【品名】2-chloro-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-ethanone

【CA登记号】

【分子式】C₁₆H₂₃ClN₂O₄

【分子量】342.8224

【元素组成】C 56.06% H 6.76% Cl 10.34% N 8.17% O 18.67%

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：(V)

The reductocondensation of 2,3,4-trimethoxybenzaldehyde (I) with ethyl piperazine-1-carboxylate (II) by means of NaBH3CN in AcOH gives the corresponding benzyl derivative (III), which is decarboxylated with aqueous KOH at 130 C yielding 1-(2,3,4-trimethoxybenzyl)piperazine (IV). The acylation of (IV) with chloroacetyl chloride in dichloromethane affords 1-(2-chloroacetyl)-4-(2,3,4-trimethoxybenzyl)piperazine (V)., which is finally condensed with diosmetin (VI) by means of KHCO3 in DMF.

参考文献中间体

合成目标

【1】 Ferté, J.; Kühnel, J.-M.; Chapuis, G.; Rolland, Y.; Lewin, G.; Schwaller, M.A.; Flavonoid-related modulators of multidrug resistance: Synthesis, pharmacological activity, and structure-activity relationships. J Med Chem 1999, 42, 3, 478.

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)	22119	2,3,4-trimethoxybenzaldehyde	2103-57-3	C₁₀H₁₂O₄	详情	详情
(II)	24694	N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine	120-43-4	C₇H₁₄N₂O₂	详情	详情
(III)	30010	ethyl 4-(2,3,4-trimethoxybenzyl)-1-piperazinecarboxylate		C₁₇H₂₆N₂O₅	详情	详情
(IV)	24354	2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether		C₁₄H₂₂N₂O₃	详情	详情
(V)	30011	2-chloro-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-ethanone		C₁₆H₂₃ClN₂O₄	详情	详情
(VI)	30012	5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one	520-34-3	C₁₆H₁₂O₆	详情	详情

Extended Information