【结 构 式】 |
【分子编号】49931 【品名】2-(4-methyl-1-piperazinyl)phenyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C18H22N2O3S 【 分 子 量 】346.45036 【元素组成】C 62.4% H 6.4% N 8.09% O 13.85% S 9.26% |
合成路线1
该中间体在本合成路线中的序号:(XVIII)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
【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 | CAS号 | 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 |