Tetrahydrofuran → 1H-Indol-3-Ylmethanamine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]#[N:17])=[CH:8]1.O1CCCC1>O1CCOCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][NH2:17])=[CH:8]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium aluminum hydride (100 mg) was added to a solution of 1H-indole-3-carbonitrile (100 mg) in 15 mL of 2:1 dioxane:tetrahydrofuran. The mixture was refluxed for 0.5 h, then cooled to 0 C and quenched by the sequential addition of 0.1 mL water, 0.1 mL 3 N sodium hydroxide, and 0.3 mL more water. After the mixture was stirred for 15 min at rt, the aluminum salts were removed by filtration and the solvent was evaporated to give 56 mg of C-(1H-indol-3-yl)methylamine.
Workup
- temperatureThe mixture was refluxed for 0.5 h
- temperaturecooled to 0 C
- customquenched by the sequential addition of 0.1 mL water, 0.1 mL 3 N sodium hydroxide, and 0.3 mL more water
- customthe aluminum salts were removed by filtration
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-51057ba33ac843df960a60de27fd9d4c
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084154B2
Reaction notes
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