1,4-Dioxane → 2,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:16]=[CH:15][C:14]2[NH:13][C:12]3[CH2:17][CH2:18][CH2:19][NH:20][C:21](=O)[C:11]=3[C:10]=2[CH:9]=1.O1CCOC[CH2:24]1>>[CH3:24][N:20]1[CH2:19][CH2:18][CH2:17][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][C:8]([CH3:7])=[CH:9][C:10]=3[C:11]=2[CH2:21]1

Participants

Reactant 3

HCID 312751,4-Dioxane

HCID 21226445Aluminium lithium hydride

HCID 287441949-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one

Product 1

HCID 248990502,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole

Procedure

Lithium aluminum hydride (3 g, 78.95 mmol) was placed in 1,4-dioxane (100 mL) under inert atmosphere and 9-methyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (3 g, 14.018 mmol) was added, and the mixture heated to reflux for 15 h. The reaction was monitored by TLC. The reaction was quenched with saturated aqueous sodium sulfate at 0° C., and the reaction mixture filtered. The filtrate was dried over anhydrous sodium sulfate and evaporated to dryness to afford solid, which was washed with water followed by EtOAc, and dried to afford 1.25 g of the title compound.