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【结 构 式】

【分子编号】23118

【品名】ethyl 3-[4-(acetamido)-2-methoxyphenoxy]propanoate

【CA登记号】

【 分 子 式 】C14H19NO5

【 分 子 量 】281.3086

【元素组成】C 59.78% H 6.81% N 4.98% O 28.44%

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)

By condensation of 3-(4-acetamido-2-methoxyphenoxy)propyl p-toluenesulfonate with 1-(2-fluorophenyl)piperazine (II). The starting products are obtained as follows: a) The addition of 4-acetamido-2-methoxyphenol (III) to ethyl acrylate (IV) gives ethyl-3-(4-acetamido-2-methoxyphenoxy)propionate (V), which is reduced with LiAlH4 to the corresponding alcohol and tosylated with tosyl chloride to the starting compound (I). b) The condensation of benzylamine (VI) with ethyl bromoacetate (VII) by means of K2CO3 gives N,N-bis(ethoxycarbonyl methyl)benzylamine (VIII), which is reduced with LiAlH4 and treated with SOCl2 to afford N,N-bis(2-chloroethyl)benzylamine (IX). The cyclization of (IX) with 2-fluoroaniline (X) yields 1-benzyl-4-(2-fluorophenyl)piperazine (XI), which is finally debenzylated by hydrogenation with H2 over PdIC to give piperazine (II).

1 Fukuchi, I.; et al.; Neurochemical study of mafoprazine, a new phenylpiperazine derivative. Jpn Pharmacol 1988, 47, 9, 51.
2 Kanno, T.; Gaino, M.; Yamamura, M.; Ishida, R.; Shintomi, K. (Tanabe Seiyaku Co., Ltd.); N-Aryl-N-phenoxy-alkyl-piperazine compounds useful in decreasing intracranial presssure. EP 0034284; JP 156115769; US 4413006 .
3 Prous, J.; Castaner, J.; Mafoprazine mesylate. Drugs Fut 1988, 13, 10, 920.
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) 23114 3-[4-(acetamido)-2-methoxyphenoxy]propyl 4-methylbenzenesulfonate C19H23NO6S 详情 详情
(II) 23115 1-(2-fluorophenyl)piperazine 1011-15-0 C10H13FN2 详情 详情
(III) 23116 N-(4-hydroxy-3-methoxyphenyl)acetamide C9H11NO3 详情 详情
(IV) 10164 ethyl acrylate 140-88-5 C5H8O2 详情 详情
(IV) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(V) 23118 ethyl 3-[4-(acetamido)-2-methoxyphenoxy]propanoate C14H19NO5 详情 详情
(VI) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(VIII) 23121 ethyl 2-[benzyl(2-ethoxy-2-oxoethyl)amino]acetate C15H21NO4 详情 详情
(IX) 23122 N-benzyl-2-chloro-N-(2-chloroethyl)-1-ethanamine; N-Benzylbis(2-chloroethyl)amine 10429-82-0 C11H15Cl2N 详情 详情
(X) 22296 2-fluorophenylamine; 2-fluoroaniline 348-54-9 C6H6FN 详情 详情
(XI) 23124 1-benzyl-4-(2-fluorophenyl)piperazine C17H19FN2 详情 详情
Extended Information