Diisopropylethylamine → 6-Chloro-4-[[1-(3-phenylprop-2-enyl)piperidin-4-yl]amino]chromen-2-one

Participants

Reaction Steps

To a solution of 1-(3-Phenyl-allyl)-piperidin-4-ylamine (4) (1.01 g,4.65 mmol) and diisopropylethylamine (1.63 mL, 9.3 mmol) in 10 mL CHCl3 was added a solution of compound 3 (1.1 g, 5.6 mmol) in 10 mL CHCl3. The reaction was stirred at room temperature for about 3 hours. The reaction mixture was then washed with water and brine and dried with MgSO4. The yellow residue was triturated with a small volume of dichloromethane and filtered. The final product was converted to the HCl salt by addition of 4.0N HCl in dioxane to a suspension of the compound in dichloromethane. The solvent was removed by evaporation and the residue triturated with methanol to give the title compound (780 mg, 39%). 1H NMR (300 MHz, MeOD-d4) δ 1.92-2.22 (2H, m), 2.35-2.45 (2H, bd, J=11.8 Hz), 3.15-3.35 (2H, m), 3.65-3.75 (2H, bd, j=12.3), 3.85-4.0 (1H, m), 3.90-4.00 (2H, d, J=6.9 Hz), 5.46 (1H, s), 6.32-6.43 (1H, p, J=7.7 Hz), 6.92-6.98 (1H, d, J=16.2 Hz), 7.31-7.41 (4H, m), 7.52-7.54 (2H, m), 7.58-7.62 (1H, dd, J=2.0, 8.8 Hz), 8.148 (1H, s).

Provenance & Evidence