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【结 构 式】 
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【分子编号】33323 【品名】N-[(E)-3-bromo-2-butenyl]-N-methyl-N-[(1R)-1-methyl-2-phenylethyl]amine; (E)-3-bromo-N-methyl-N-[(1R)-1-methyl-2-phenylethyl]-2-buten-1-amine 【CA登记号】 |
【 分 子 式 】C14H20BrN 【 分 子 量 】282.22354 【元素组成】C 59.58% H 7.14% Br 28.31% N 4.96% |
合成路线1
该中间体在本合成路线中的序号：(II)Compound can be prepared in several related ways: 1) The condensation of N-(1-phenylisopropyl)methylamine (I) with 1,2-dibromopropene (A) by heating at 100 C gives N-(1-phenylisopropyl)-N-methyl-2-bromopropenylamine (II), which is then dehydrobrominated and isomerized by treating with KOH in refluxing ethanol water. 2) By heating a mixture of (I) and propargyl bromide (B) at 100 C. 3) By reductocondensation of (I) with propargyl aldehyde (C) by means of amalgamated Al in ethanol. 4) By condensation of (I) with formaldehyde and acetylene by means of CuCl in hot dioxane. 5) By condensation of 1-phenylisopropyl chloride (III) with N-methylpropargylamine (IV) by heating at 80 C in a sealed tube.
| 【1】 Ecsery, Z.; et al.; AT 252901 . |
| 【2】 Ecsery, Z.; et al.; AT 251560 . |
| 【3】 Ecsery, Z.; et al.; Verfahren zur Herstellung von Phenylisopropylaminen. DE 1568277; NL 6605956 . |
| 【4】 Ecsery, Z.; et al.; Verfahren zur Herstellung von Phenylisopropylaminen. CH 530953; DE 1227447 . |
| 【5】 Roberts, P.J.; Castaner, J.; Selegiline. Drugs Fut 1979, 4, 2, 128. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 23634 | acetylene | 74-86-2 | C2H2 | 详情 | 详情 | |
| (B) | 11176 | 3-Bromopropyne; 3-Bromo-1-propyne | 106-96-7 | C3H3Br | 详情 | 详情 |
| (A) | 33322 | (E)-1,2-dibromo-1-propene | 26391-16-2 | C3H4Br2 | 详情 | 详情 |
| (I) | 33321 | N-methyl-N-[(1R)-1-methyl-2-phenylethyl]amine; (2R)-N-methyl-1-phenyl-2-propanamine | 537-46-2 | C10H15N | 详情 | 详情 |
| (II) | 33323 | N-[(E)-3-bromo-2-butenyl]-N-methyl-N-[(1R)-1-methyl-2-phenylethyl]amine; (E)-3-bromo-N-methyl-N-[(1R)-1-methyl-2-phenylethyl]-2-buten-1-amine | C14H20BrN | 详情 | 详情 | |
| (III) | 33324 | 1-[(2R)-2-chloropropyl]benzene | C9H11Cl | 详情 | 详情 | |
| (IV) | 33325 | N-methyl-2-propyn-1-amine; N-methyl-N-(2-propynyl)amine | C4H7N | 详情 | 详情 | |
| (C) | 23544 | propiolaldehyde | C3H2O | 详情 | 详情 |