N-[[4-(benzyloxy)-1H-indol-2-yl]methyl]-N,N-dimethylamine; [4-(benzyloxy)-1H-indol-2-yl]-N,N-dimethylmethanamine -Drug Synthesis Database

【结构式】

【分子编号】33539

【品名】N-[[4-(benzyloxy)-1H-indol-2-yl]methyl]-N,N-dimethylamine; [4-(benzyloxy)-1H-indol-2-yl]-N,N-dimethylmethanamine

【CA登记号】

【分子式】C₁₈H₂₀N₂O

【分子量】280.36968

【元素组成】C 77.11% H 7.19% N 9.99% O 5.71%

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：(IV)

4-Benzyloxy-indole-2-carboxylic acid (I) is converted into the corresponding dimethylamide (III), via the corresponding acid chloride (II); the dimethylamide (III) is reduced with LiAlH4 to give 4-benzyloxy-2-dimethylaminomethyl-indole (IV), which is hydrogenated to 4-hydroxy-2-methyl-indole (V). The reaction of (V) with epichlorohydrin (A) in aqueous NaOH gives the crude epoxide which without isolation is treated with isopropylamine (B) in refluxing dioxane.

参考文献中间体

合成目标

【1】 Seemann, F.; et al.; Synthetic indoles. 10. Chemistry of 4-hydroxy-indoles. Helv Chim Acta 1971, 54, 8, 2411-19.
【2】 Troxler, F.; Hofmann, A.; Verfahren zur Herstellung neuer Indolderivate. AT 316542B; CH 502337 .
【3】 Troxler, F.; Hofmann, A.; Verfahren zur Herstellung neuer Indolderivate. CH 543505 .
【4】 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
(I)	33536	4-(benzyloxy)-1H-indole-2-carboxylic acid		C₁₆H₁₃NO₃	详情	详情
(II)	33537	4-(benzyloxy)-1H-indole-2-carbonyl chloride		C₁₆H₁₂ClNO₂	详情	详情
(III)	33538	4-(benzyloxy)-N,N-dimethyl-1H-indole-2-carboxamide		C₁₈H₁₈N₂O₂	详情	详情
(IV)	33539	N-[[4-(benzyloxy)-1H-indol-2-yl]methyl]-N,N-dimethylamine; [4-(benzyloxy)-1H-indol-2-yl]-N,N-dimethylmethanamine		C₁₈H₂₀N₂O	详情	详情
(V)	33540	4-Hydroxy-2-methylindole; 2-Methyl-1H-indol-4-ol	35320-67-3	C₉H₉NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

4-Hydroxy-2-methyl-indole (IV) can be quaternized with MeI yielding the ammonium salt (VI), which by heating with aqueous NaCN in converted into 2-cyanomethyl-4-benzyloxyindole (VII). The hydrolysis of (VII) affords the corresponding acid (VIII), which is decarboxylated to 4-benzyloxy-2-methyl-indole (IX). Finally, this compound is hydrogenated to the previously obtained 4-hydroxy-2-methyl-indole (V).

参考文献中间体

合成目标

【1】 Troxler, F.; Hofmann, A.; Verfahren zur Herstellung neuer Indolderivate. AT 316542B; CH 502337 .
【2】 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
(IV)	33539	N-[[4-(benzyloxy)-1H-indol-2-yl]methyl]-N,N-dimethylamine; [4-(benzyloxy)-1H-indol-2-yl]-N,N-dimethylmethanamine		C₁₈H₂₀N₂O	详情	详情
(V)	33540	4-Hydroxy-2-methylindole; 2-Methyl-1H-indol-4-ol	35320-67-3	C₉H₉NO	详情	详情
(VI)	33541	[4-(benzyloxy)-1H-indol-2-yl]-N,N,N-trimethylmethanaminium iodide		C₁₉H₂₃IN₂O	详情	详情
(VII)	33542	2-[4-(benzyloxy)-1H-indol-2-yl]acetonitrile		C₁₇H₁₄N₂O	详情	详情
(VIII)	33543	2-[4-(benzyloxy)-1H-indol-2-yl]acetic acid		C₁₇H₁₅NO₃	详情	详情
(IX)	33544	benzyl 2-methyl-1H-indol-4-yl ether; 4-(benzyloxy)-2-methyl-1H-indole		C₁₆H₁₅NO	详情	详情

Extended Information