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【结 构 式】 
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【分子编号】55283 【品名】1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-amine; N-{3-[5-amino-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propyl}-N,N-dimethylamine 【CA登记号】 |
【 分 子 式 】C19H23FN2O 【 分 子 量 】314.4029032 【元素组成】C 72.58% H 7.37% F 6.04% N 8.91% O 5.09% |
合成路线1
该中间体在本合成路线中的序号：(VI)The Grignard reaction of 5-aminophthalide (I) with 4-fluorophenylmagnesium bromide (II) in THF gives the methanone (III), which is submitted to a new Grignard reaction with 3-(dimethylamino)propylmagnesium chloride (IV) in the same solvent to yield 1-[4-amino-2-(hydroxymethyl)phenyl]-4-(dimethylamino)-1-(4-fluorophenyl)-1-butanol (V). The cyclization of (V) by heating in H3PO4 affords the isobenzofuran derivative (VI), which is finally submitted to diazotation with NaNO2 and H2SO4 , followed by reaction with NaCN.
| 【1】 Bregnedal, P.; Petersen, H.; Bogeso, K.P. (H. Lundbeck A/S); Method for the preparation of citalopram. US 6258842; WO 9819512 . |
| 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) | 55280 | 5-amino-2-benzofuran-1(3H)-one | C8H7NO2 | 详情 | 详情 | |
| (II) | 13643 | 4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide | 352-13-6 | C6H4BrFMg | 详情 | 详情 |
| (III) | 55281 | [4-amino-2-(hydroxymethyl)phenyl](4-fluorophenyl)methanone | C14H12FNO2 | 详情 | 详情 | |
| (IV) | 12587 | Chloro[3-(dimethylamino)propyl]magnesium | C5H12ClMgN | 详情 | 详情 | |
| (V) | 55282 | 1-[4-amino-2-(hydroxymethyl)phenyl]-4-(dimethylamino)-1-(4-fluorophenyl)-1-butanol | C19H25FN2O2 | 详情 | 详情 | |
| (VI) | 55283 | 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-amine; N-{3-[5-amino-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propyl}-N,N-dimethylamine | C19H23FN2O | 详情 | 详情 |