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【结 构 式】 
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【分子编号】23116 【品名】N-(4-hydroxy-3-methoxyphenyl)acetamide 【CA登记号】 |
【 分 子 式 】C9H11NO3 【 分 子 量 】181.19128 【元素组成】C 59.66% H 6.12% N 7.73% O 26.49% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |