Sodium Sulfate → HCID 19936680, compound

Participants

Reaction Steps

A solution of 3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indole-5-carboxamide (3.2 g, prepared in Example 73) in dry THF (40 ml) is added dropwise at 0° C. to a suspension of lithium aluminum hydride (LiAlH4, 1.2 g) in anhydrous THF (200 ml). After 10 hours at room temperature, the reaction mixture is hydrolyzed at 0° C. by the addition of a saturated solution of sodium sulfate. After filtration on Celite, the solution is concentrated, taken up with ether and extracted with a dilute solution of hydrochloric acid. The aqueous phase is rendered basic with sodium hydroxide and extracted with methylene chloride. The organic phase is dried over sodium sulfate and concentrated. After chromatography on silica gel (eluent: AcOEt), 3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indole-5-methanamine (1.8 g) is obtained in the form of a yellowish solid.

Provenance & Evidence