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【结 构 式】 
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【分子编号】33545 【品名】1-(benzylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol 【CA登记号】 |
【 分 子 式 】C19H22N2O2 【 分 子 量 】310.39596 【元素组成】C 73.52% H 7.14% N 9.03% O 10.31% |
合成路线1
该中间体在本合成路线中的序号：(XI)The reaction of 4-hydroxy-2-methyl-indole (V) with 1-(N-benzylisopropylamino)-3-chloro-2-propanol (D) by means of NaOH in refluxing aqueous dioxane yields the corresponding benzylamine (X), which is debenzylated by catalytic hydrogenation. The reaction of 4-hydroxy-2-methyl-indole (V) with epichlorohydrin (A) and benzylamine (B) gives 4-(3-benzylamino-2-hydroxypropoxy)-2-methyl-indole (XI), which is debenzylated by hydrogenolysis to 4-(3-amino-2-hydroxypropoxy)-2-methyl-indole (XII). The condensation of (XII) with refluxing acetone (C) affords the corresponding N-isopropylidene derivative (XIII), which is finally hydrogenated with H2 over Pd/C in methanol.
| 【1】 Seemann, F.; et al.; Synthetic indoles. 10. Chemistry of 4-hydroxy-indoles. Helv Chim Acta 1971, 54, 8, 2411-19. |
| 【2】 Troxler, F.; Verfahren zur Herstellung neuer Indolderivate. CH 472404; ES 337457 . |
| 【3】 Troxler, F.; Verfahren zur Herstellung neuer Indolderivate. CH 469002; ES 337458 . |
| 【4】 Troxler, F.; Verfahren zur Herstellung von neuem 4-(2-Hydroxy-3-isopropylaminopropoxy)-2-methylindol und seiner Saureadditionssalze Indolderivate. AT 317199 . |
| 【5】 Weetman, D.F.; Castaner, J.; Mepindolol. Drugs Fut 1978, 3, 5, 381. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (B) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (D) | 33549 | 1-[benzyl(isopropyl)amino]-3-chloro-2-propanol | C13H20ClNO | 详情 | 详情 | |
| (V) | 33540 | 4-Hydroxy-2-methylindole; 2-Methyl-1H-indol-4-ol | 35320-67-3 | C9H9NO | 详情 | 详情 |
| (X) | 33548 | 1-[benzyl(isopropyl)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol | C22H28N2O2 | 详情 | 详情 | |
| (XI) | 33545 | 1-(benzylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol | C19H22N2O2 | 详情 | 详情 | |
| (XII) | 33546 | 1-amino-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol | C12H16N2O2 | 详情 | 详情 | |
| (XIII) | 33547 | 1-[(1-methylethylidene)amino]-3-[(2-methyl-1H-indol-4-yl)oxy]-2-propanol | C15H20N2O2 | 详情 | 详情 | |
| (C) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |