Potassium Carbonate → Phthalimide

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-methoxy-2-(R,S)-methylamino-1,2,3,4-tetrahydronaphthalene (3.02 g, 15.9 mmol), N-(4-bromobutyl)phthalimide (4.82 g, 17.1 mmol), anhydrous potassium carbonate (4.80 g, 34.7 mmol) and dry dimethylformamide (75 ml) was heated at 60° C. for 2 h, then left at room temperature for 18 h. Excess solvent was evaporated in vacuo, and the residue was partitioned between water (200 ml) and dichloromethane (3×100 ml). The organic phase was dried (Na2SO4) then evaporated in vacuo to give an oil. Chromatography on silica with 0-5% methanol-dichloromethane elution gave the intermediate phthalimide (3.8 g) as an oil which solidified. The latter was dissolved in ethanol (20 ml) and treated with hydrazine hydrate (2 ml; excess). Stirring at room temperature was carried out for 18 h, followed by reflux for 1 h. The mixture was cooled to 0° C., then filtered. The filtrate was evaporated in vacuo and the residue dissolved in dichloromethane (50 ml). Anhydrous sodium sulfate was added, and the mixture was filtered through kieselguhr. The filtrate was evaporated in vacuo to give the title compound (1.90 g, 46%).

Provenance & Evidence