Dimethylformamide → HCID 22890651, compound

Participants

Reaction Steps

To a solution of the product from Example 156B (0.35 g, 0.838 mmol) in N,N-dimethylformamide (3.0 mL) was added piperidine (0.17 mL, 1.72 mmol), and this mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between dichloromethane and water. The isolated organic layer was washed with brine and dried over MgSO4, filtered and evaporated. The residue dissolved in water (1.0 mL) and concentrated sulfuric acid (0.10 mL) was added at room temperature, followed by heating to 50° C. A solution of sodium nitrite (0.25 g) in water (0.60 mL) was added dropwise at 50° C. and the reaction was stirred for 1 hour. The reaction was extracted with ethyl acetate and washed with water and brine. The organic was dried over MgSO4, filtered and evaporated to give the crude product (0.041 g, 25% yield), which was used without further purification.

Provenance & Evidence