HCID 13324711, compound → HCID 13324728, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 1.67 g of lithium aluminum hydride in 100 ml of dry tetrahydrofuran (THF), kept at 0°-5° C. under nitrogen, was added dropwise a solution of 5.60 g (0.022 mole) of 3-(5-chloro-1-indolyl)benzonitrile of Example 6a in 150 ml of THF. The mixture was stirred 1 hour more at 0° C., 1 hour at room temperature, and then refluxed for 5 hours. After cooling to 0° C., the reaction was quenched by slow and cautious addition of a solution of 25 ml of water in 25 ml of THF. The resulting mixture was stirred 1 hour at room temperature before filtering to remove the inorganic salts. The filtrate was concentrated to an oily residue which was partitioned between 250 ml of dichloromethane and 250 ml of water. The organic phase was separated and extracted twice more with water before drying over Na2SO4 and concentrating to an oil (5.8 g). This was dissolved in 20 ml of absolute ethanol and the stirred solution treated with 100 ml of ethereal hydrogen chloride. The salt was collected and found to weigh 5.2 g (81% overall yield) m.p. 195° C.-sinter, 220°-228° C. melting. Recrystallization from boiling ethanol (charcoal) furnished 2.4 g (37% yield) of 3-(5-chloro-1-indolyl)benzenemethanamine hydrochloride, m.p. 230°-233° C.

Provenance & Evidence