Tetrahydrofuran → 1H-Indol-3-Ylmethanamine

HRID 6737

Reaction equation

HRID 6737 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]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2302823-CyanoindoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 4721071H-Indol-3-YlmethanamineYield 54.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. temperatureThe mixture was refluxed for 0.5 h
  2. temperaturecooled to 0 C
  3. customquenched by the sequential addition of 0.1 mL water, 0.1 mL 3 N sodium hydroxide, and 0.3 mL more water
  4. customthe aluminum salts were removed by filtration
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-51057ba33ac843df960a60de27fd9d4c
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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