Dichloromethane → 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-N-methylpentanamide

Participants

Reaction Conditions

Reaction Steps

5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-pentanoic acid (0.12 g, 0.21 mmol) prepared in Example 128 was mixed with dichloromethane (5 ml), N,N-dimethylformamide (100 μl) and thionyl chloride (24 μl). The resulting mixture was stirred at 50° C. for 30 minutes and then cooled on ice, followed by addition of a 40% methylamine/methanol solution (1 ml), and stirring was continued at room temperature for an additional 4 hours. The reaction mixture was partitioned between ethyl acetate and saturated brine, washed and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/4) to give the titled compound (0.10 g, yield: 83%) as a white crystal (cis:trans=4:1).

Provenance & Evidence