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Example 10 Preparation of 1H-indole-4-methanamine Lithium aluminum hydride (3.80 g, 100.0 mmol) was added in 0.5 g portions over 30 min to a solution of 1H-indole-4-carbonitrile (prepared according to Clark, Robin D.; Repke, David B. J. Heterocycl. Chem. 1985, 22, 121-5; 7.50 g, 52.8 mmol) in tetrahydrofuran (250 mL). The mixture was heated at reflux for 30 min. A solution of 1 M sodium hydroxide was added to quench excess lithium aluminum hydride. The mixture was filtered and the filter cake was washed with water. The filtrate was first made acidic with 1 N HCl and then made basic again by the addition of saturated aqueous NaHCO3. The water layer was then extracted with nBuOH. Evaporation of nBuOH, and drying under vacuum gave 1H-indole-4-methanamine (6.24 g, 80%) as a beige solid.
Preparation of C-(1H-indol-4-yl)-methylamine To a solution of 4-cyanoindole (7.5 g, 53 mmol) in THF (100 ml) was added at rt a 1.0M solution of lithium aluminum hydride in THF (100 ml, 100 mmol). The mixture was refluxed for 30 min then cooled to rt. The reaction mixture was quenched with 1N NaOH and filtered. The filtrate was acidified with 1N HCl and stirred at rt for 10 min. The pH was adjusted to ~8 by adding sat NaHCO3 and extracted with n-butanol. The layers were separated and the organic layer was concentrated to dryness. The residue was triturated with methanol. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to afford the desired product as a solid that was further dried under high vacuum at 50 C. (7.27 g, 94% yield).
82%
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2068.65 - 2172.08 Torr;Inert atmosphere;
Method B. 4-cynoindole (1.0 mmol) was dissolved in MeOH in a hydrogenator reaction flask, 10% Pd/C (10 mg) was added and hydrogenator was shook at 40-42 psi overnight. Reaction mixture was carefully taken out from hydrogenator, filtered through celite and purified by column chromatography (EtOAc: MeOH; 9.5: 0.5) with few drops of aqueous ammonia.
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