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【结 构 式】 
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【分子编号】48850 【品名】N-benzyl-N-[3,3-bis(3-fluorophenyl)-2-propenyl]-N-methylamine; N-benzyl-3,3-bis(3-fluorophenyl)-N-methyl-2-propen-1-amine 【CA登记号】 |
【 分 子 式 】C23H21F2N 【 分 子 量 】349.4232864 【元素组成】C 79.06% H 6.06% F 10.87% N 4.01% |
合成路线1
该中间体在本合成路线中的序号：(VI)Treatment of ethyl acrylate (I) with N-benzylmethylamine (II) affords aminopropionate derivative (III), which is then subjected to Grignard reaction with 3-bromoflurobenzene (IV) by means of Mg and catalytic iodine in refluxing THF and crystallized as a hydrochloride salt by treatment with HCl to provide propylamino derivative (V). Alcohol (V) is converted into allylamine (VI) by elimination induced by heating with HCl/HOAc, and finally the target product is obtained by hydrogenation of (VI) catalyzed by Pd(OH)2/C in EtOH.
| 【1】 Moe, S.; Mueller, A.; Balandrin, M. (NPS Pharmaceuticals, Inc.); Methods and cpds. for treating depression and other disorders. EP 1096926; WO 0002551 . |
| 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) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (II) | 11969 | N-Methyl(phenyl)methanamine; N-Benzyl-N-methylamine; N-Methylbenzylamine | 103-67-3 | C8H11N | 详情 | 详情 |
| (III) | 48848 | ethyl 3-[benzyl(methyl)amino]propanoate | C13H19NO2 | 详情 | 详情 | |
| (IV) | 28002 | 1-bromo-3-fluorobenzene; 3-Bromofluorobenzene | 1073-06-9 | C6H4BrF | 详情 | 详情 |
| (V) | 48849 | 3-[benzyl(methyl)amino]-1,1-bis(3-fluorophenyl)-1-propanol | C23H23F2NO | 详情 | 详情 | |
| (VI) | 48850 | N-benzyl-N-[3,3-bis(3-fluorophenyl)-2-propenyl]-N-methylamine; N-benzyl-3,3-bis(3-fluorophenyl)-N-methyl-2-propen-1-amine | C23H21F2N | 详情 | 详情 |