Sodium sulfate decahydrate → HCID 22181195, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (230 mg) in tetrahydrofuran (5 ml) was added dropwise a solution of 4-(1-acetylpiperidin-4-yloxy)-3-chloroaniline obtained in reference example 10 in tetrahydrofuran (10 ml) with stirring under ice-cooling in a nitrogen atmosphere, and the resulting mixture was refluxed for 3.5 hours. After refluxing, to the reaction mixture was furthermore added lithium aluminum hydride (115 mg), and the resulting mixture was refluxed for a further 2 hours. After cooling to room temperature, to the reaction mixture was added sodium sulfate decahydrate, and the resulting mixture was furthermore stirred at room temperature overnight. After removing insoluble materials by filtration, the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (3:1˜1:2) as the eluent to afford the title compound (448 mg, yield: 58%) as a brown oil.

Provenance & Evidence