9H-carbazol-4-yl 2-oxiranylmethyl ether; 4-(2-oxiranylmethoxy)-9H-carbazole -Drug Synthesis Database

【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 合成路线2

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

参考文献中间体

合成目标

【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.

参考文献中间体

合成目标

【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