HRID1633130

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID25517

未命名化合物

结构：COC(=O)CCCCCn1c(-c2cccnc2)c(C)c2cc(Cl)ccc21

HCID13362109

未命名化合物

HCID21226445

未命名化合物

PRODUCTS

生成物

结构：Cc1c(-c2cccnc2)n(CCCCCCO)c2ccc(Cl)cc12.Cc1c(-c2cccnc2)n(CCCCCCO)c2ccc(Cl)cc12.Cl.Cl.O

HCID70506192

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

To a suspension of 0.49 g of lithium aluminum hydride in 50 ml of anhydrous tetrahydrofuran under nitrogen is added dropwise at room temperature a solution of 3.92 g of 1-(5-methoxycarbonylpentyl)-5-chloro-3-methyl-2-(3-pyridyl)indole in 30 ml of anhydrous tetrahydrofuran. After addition is complete the suspension is stirred for 1 hour at room temperature, and 50 ml of a saturated ammonium chloride solution is added. The reaction mixture is allowed to stand at room temperature overnight and the organic layer is separated. The aqueous layer is filtered to remove salts and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by trituration with hexane/ether and dissolved in ethanol. Ethanolic hydrochloric acid is added to acidity and the solution diluted with anhydrous ether to crystallize the product. 1-(6-Hydroxyhexyl)-5-chloro-3-methyl-2-(3-pyridyl)indole hydrochloride hemihydrate, m.p. 115°-118°, is obtained.

WORKUP

后处理

additionAfter addition
waitto stand at room temperature overnight
customthe organic layer is separated
filtrationThe aqueous layer is filtered
customto remove salts
extractionextracted with ethyl acetate (2×50 ml)
washThe combined organic layers are washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product is purified by trituration with hexane/ether
dissolutiondissolved in ethanol
additionEthanolic hydrochloric acid is added to acidity
additionthe solution diluted with anhydrous ether
customto crystallize the product

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3cd0ab5ac39f47da8d83ea5fa44d56b7
来源数据集: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04478842
来源说明: uspto-grants-1984_10

反应 SMILES

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[C:18]([CH3:26])=[C:17]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=O.[Cl-:33].[NH4+]>O1CCCC1>[OH2:8].[ClH:25].[OH:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[C:18]([CH3:26])=[C:17]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.[OH:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[C:18]([CH3:26])=[C:17]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.[ClH:33]