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【结 构 式】

【分子编号】40171

【品名】9H-carbazol-4-yl 2-oxiranylmethyl ether; 4-(2-oxiranylmethoxy)-9H-carbazole

【CA登记号】51997-51-4

【 分 子 式 】C15H13NO2

【 分 子 量 】239.27376

【元素组成】C 75.3% H 5.48% N 5.85% O 13.37%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

By condensation of 4-hydroxycarbazole (I) with epichlorohydrin (II) by means of NaOH in aqueous dioxane at 40 C to yield 4-(2,3-epoxypropoxy)carbazole (III), followed by treatment with isopropylamine (IV) in refluxing ethanol

1 Weetman, D.F.; Castaner, J.; Carazolol. Drugs Fut 1977, 2, 11, 715.
2 Leinert, H.; et al. (Boehringer Ingelheim GmbH); Triyclic diphenylamines derivatives. CH 598216; DE 2240599; FR 2196165; GB 1369580; JP 49056973 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 29480 4-Hydroxycarbazole; 9H-carbazol-4-ol 52602-39-8 C12H9NO 详情 详情
(II) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(III) 40171 9H-carbazol-4-yl 2-oxiranylmethyl ether; 4-(2-oxiranylmethoxy)-9H-carbazole 51997-51-4 C15H13NO2 详情 详情
(IV) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VIII)

This compound has been obtained in two related ways: 1. The reaction of 2-(2-bromoethoxy)anisole (I) with benzylamine (II) by heating at 80 C gives the secondary amine (III), which is condensed with epichlorohydrin (IV) by heating at 60 C to yield the isopropanol derivative (V). The condensation of (V) with 4-hydroxycarbazole (VI) by means of K2CO3 in refluxing dioxane affords the adduct (VII), which is finally debenzylated by hydrogenolysis with H2 over Pd/C in ethanol/water. 2. The condensation of the secondary amine (III) with 4-(2,3-epoxypropoxy)carbazole (VIII) in refluxing ethanol gives the already reported adduct (VII), which is debenzylated as indicated.

1 Seres, P.; Cselenyak, J.; Nagy, K.; Simig, G.; Gregor, T.; Nagy, P.K.; Greff, Z.; Balazs, L.; Barkoczy, J.; Vereczkey, G.D.; Nemeth, N.; Szabo, T.; Ratkai, Z.; Doman, I. (Egis Pharmaceuticals Ltd.); Process and intermediates for preparing 1-[9'H-carbazol-4'-yloxy]-3-[2''-(2'''-methoxy-phenoxy)ethyl]amino]-propan-2-ol (carvedilol). EP 0918055 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51402 2-(2-Bromoethoxy)methoxybenzene; 1-Bromo-2-(2-methoxyphenoxy)ethane 4463-59-6 C9H11BrO2 详情 详情
(II) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(III) 30528 N-benzyl-2-(2-methoxyphenoxy)-1-ethanamine; N-benzyl-N-[2-(2-methoxyphenoxy)ethyl]amine C16H19NO2 详情 详情
(IV) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(V) 51403 1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-chloro-2-propanol C19H24ClNO3 详情 详情
(VI) 29480 4-Hydroxycarbazole; 9H-carbazol-4-ol 52602-39-8 C12H9NO 详情 详情
(VII) 51404 1-[benzyl[2-(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)-2-propanol C31H32N2O4 详情 详情
(VIII) 40171 9H-carbazol-4-yl 2-oxiranylmethyl ether; 4-(2-oxiranylmethoxy)-9H-carbazole 51997-51-4 C15H13NO2 详情 详情
Extended Information