2-(1-piperazinyl)phenol -Drug Synthesis Database

【结构式】

【分子编号】49928

【品名】2-(1-piperazinyl)phenol

【CA登记号】

【分子式】C₁₀H₁₄N₂O

【分子量】178.23404

【元素组成】C 67.39% H 7.92% N 15.72% O 8.98%

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：(XV)

Acylation of 2-(1-piperazinyl)phenol (XV) with ethyl chloroformate produced the carbamate (XVI). After protection of the phenolic hydroxyl of (XVI) as the corresponding tosylate (XVII), reduction of the carbamate group of (XVII) with LiAlH4 gave rise to the N-methylpiperazine (XVIII). The tosylate group of (XVIII) was then removed by hydrolysis with KOH in aqueous ethanol, yielding phenol (XIX). The Williamson's ether synthesis between phenol (XIX) and bromide (XIV) provided adduct (XX). Finally, basic hydrolysis of the ester group of (XX) furnished the title carboxylic acid

参考文献中间体

合成目标

【1】 Cimetiere, B.; et al.; Discovery of new combined 5-HT2 and TP-receptor antagonists. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 57.
【2】 Verbeuren, T.; Simonet, S.; Descombes, J.-J.; Cimetiere, B.; Lavielle, G. (ADIR et Cie.); Benzenesulfonamide derivs., process for their preparation and pharmaceutical compsns. containing them. EP 1118610; FR 2803848; JP 2001226353 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIV)	49927	methyl 3-(3-(bromomethyl)-6-[[(4-chlorophenyl)sulfonyl]amino]-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate	C₂₁H₂₃BrClNO₄S	详情	详情
(XV)	49928	2-(1-piperazinyl)phenol	C₁₀H₁₄N₂O	详情	详情
(XVI)	49929	ethyl 4-(2-hydroxyphenyl)-1-piperazinecarboxylate	C₁₃H₁₈N₂O₃	详情	详情
(XVII)	49930	ethyl 4-(2-[[(4-methylphenyl)sulfonyl]oxy]phenyl)-1-piperazinecarboxylate	C₂₀H₂₄N₂O₅S	详情	详情
(XVIII)	49931	2-(4-methyl-1-piperazinyl)phenyl 4-methylbenzenesulfonate	C₁₈H₂₂N₂O₃S	详情	详情
(XIX)	49932	2-(4-methyl-1-piperazinyl)phenol	C₁₁H₁₆N₂O	详情	详情
(XX)	49933	methyl 3-(6-[[(4-chlorophenyl)sulfonyl]amino]-3-[[2-(4-methyl-1-piperazinyl)phenoxy]methyl]-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate	C₃₂H₃₈ClN₃O₅S	详情	详情

Extended Information