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【结 构 式】 
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【分子编号】37566 【品名】2-(1H-indol-3-yl)-1,1-dimethylethylamine; 1-(1H-indol-3-yl)-2-methyl-2-propanamine 【CA登记号】 |
【 分 子 式 】C12H16N2 【 分 子 量 】188.27252 【元素组成】C 76.55% H 8.57% N 14.88% |
合成路线1
该中间体在本合成路线中的序号：(I)By reaction of 3-(2-methyl-2-aminopropyl)indole (I) and 2-(2,3-epoxypropoxy)benzonitrile (II) by heating at 120-40 C followed by a treatment with HCl in ethanol. The starting products are obtained as follows: 1) The reaction of 3-(dimethylaminomethyl)indole (III) with 2-nitropropane (IV) by means of KOH gives 3-(2-methyl-2-nitropropyl)indole (V), which is then reduced with hydrazine and Raney-Ni in ethanol to yield (I). 2) The reaction of 2-hydroxybenzonitrile (VI) with epichlorohydrin (VII) by means of piperidine affords 2-(3-chloro-2-hydroxypropoxy)benzonitrile (VIII), which is epoxidized again to (II) by treatment with NaOH in hot THF-water.
| 【1】 Kreighbaum, W.E.; et al.; Antihypertensive indole derivatives of phenoxypropanolamines with beta-adrenergic receptor antagonist and vasodilating activity. J Med Chem 1980, 23, 3, 285-289. |
| 【2】 Weetman, D.F.; Castaner, J.; Bucindolol Hydrochloride. Drugs Fut 1981, 6, 7, 405. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10158 | Piperidine | 110-89-4 | C5H11N | 详情 | 详情 | |
| (I) | 37566 | 2-(1H-indol-3-yl)-1,1-dimethylethylamine; 1-(1H-indol-3-yl)-2-methyl-2-propanamine | C12H16N2 | 详情 | 详情 | |
| (II) | 37567 | 2-(2-oxiranylmethoxy)benzonitrile | C10H9NO2 | 详情 | 详情 | |
| (III) | 37568 | N,N-Dimethyl-1H-indole-3-methanamine;Gramine;N-(1H-indol-3-ylmethyl)-N,N-dimethylamine; 3-(dimethylaminomethyl)-indole[;]1H-indol-3-yl-N,N-dimethylmethanamine | 87-52-5 | C11H14N2 | 详情 | 详情 |
| (IV) | 21819 | 2-nitropropane | 79-46-9 | C3H7NO2 | 详情 | 详情 |
| (V) | 37569 | 3-(2-methyl-2-nitropropyl)-1H-indole | C12H14N2O2 | 详情 | 详情 | |
| (VI) | 21990 | 2-hydroxybenzonitrile | 611-20-1 | C7H5NO | 详情 | 详情 |
| (VII) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (VIII) | 37570 | 2-(3-chloro-2-hydroxypropoxy)benzonitrile | C10H10ClNO2 | 详情 | 详情 |