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【结 构 式】 
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【分子编号】64675 【品名】N-[(E)-1-ethyl-1,4-diphenyl-3-butenyl]-N-methylcyclopropanecarboxamide 【CA登记号】 |
【 分 子 式 】C23H27NO 【 分 子 量 】333.47352 【元素组成】C 82.84% H 8.16% N 4.2% O 4.8% |
合成路线1
该中间体在本合成路线中的序号：(+)-(VIII)2) Igmesine has been synthesized as follows: Hydrolysis of the previously described isocyanate (V) with HCl in refluxing THF/water gives the corresponding amine (IX), which is submitted to optical resolution with L-(-)tartaric acid, yielding the (+)-isomer (+)-(IX). The acylation of (+)-(IX) with formic acid and carbonyldiimidazole (CDI) affords the expected formamide (+)-(X), which is reduced with AlAl3/LiAlH4 in THF/ethyl ether, giving (-)-N-(1-ethyl-1,4-diphenyl-3-butenyl)-N-metylamine (-)-(VI). The condensation of (-)-(VI) with cyclopropanecarbonyl chloride (VII) by means of triethylamine in dichloromethane yields the corresponding amide (+)-(VIII), which is finally reduced with AlCl3/LiAlH4 in THF/ethyl ether.
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【1】
Sorbera, L.A.; Castaner, J.; Silvestre, J.S.; Igmesine Hydrochloride |
| 【2】 Aubard, G.; Calvet, A.; Gouret, C.; Grouhel, A.; Jacobelli, H.; Junien, J.-L. (Jouveinal SA); Disubstituted benzylamines, process for their preparation, their use as medicament and their synthesis intermediates. EP 0361990; EP 0362001; FR 2636625; US 5034419; US 5089639 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (+)-(IX) | 64672 | (E)-1-ethyl-1,4-diphenyl-3-butenylamine; (E)-3,6-diphenyl-5-hexen-3-amine | C18H21N | 详情 | 详情 | |
| (+)-(X) | 64673 | (E)-1-ethyl-1,4-diphenyl-3-butenylformamide | C19H21NO | 详情 | 详情 | |
| (-)-(VI) | 64674 | (E)-N-methyl-3,6-diphenyl-5-hexen-3-amine; N-[(E)-1-ethyl-1,4-diphenyl-3-butenyl]-N-methylamine | C19H23N | 详情 | 详情 | |
| (+)-(VIII) | 64675 | N-[(E)-1-ethyl-1,4-diphenyl-3-butenyl]-N-methylcyclopropanecarboxamide | C23H27NO | 详情 | 详情 | |
| (V) | 21134 | 1-[(E)-1-ethyl-1-isocyanato-4-phenyl-3-butenyl]benzene; (E)-1-ethyl-1,4-diphenyl-3-butenyl isocyanate | C19H19NO | 详情 | 详情 | |
| (VII) | 14061 | Cyclopropanecarbonyl chloride; Cyclopropanecarboxylic acid chloride | 4023-34-1 | C4H5ClO | 详情 | 详情 |
| (IX) | 21138 | (rac)-(E)-3,6-diphenyl-5-hexen-3-amine; (rac)-[(E)-1-ethyl-1,4-diphenyl-3-butenylamine] | C18H21N | 详情 | 详情 |