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【结 构 式】

【分子编号】33549

【品名】1-[benzyl(isopropyl)amino]-3-chloro-2-propanol

【CA登记号】

【 分 子 式 】C13H20ClNO

【 分 子 量 】241.76064

【元素组成】C 64.59% H 8.34% Cl 14.66% N 5.79% O 6.62%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(D)

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
Extended Information