Sodium hydride → 4-[(2,4-dichlorophenyl)amino]-3-{2-[4-(1-ethoxyethoxy)phenyl]-1-methyl-2-oxoethyl}-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one

Participants

Reaction Steps

4-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one (450 mg, 1.323 mmol) suspended in THF (7 ml) was added during 15 min to NaH (67 mg, 2.645 mmol) suspended in THF (5 ml) at 5° C. under nitrogen. After the resulting mixture had been stirred at 0° C. for 1 h tetrabutylammonium iodide (49 mg, 0.132 mmol) was added followed by dropwise addition of 2-bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-one (597 mg, 1.984 mmol) dissolved in THF (5 ml) during 15 min. After the addition the cooling bath was removed and the reaction was continued at rt overnight. Water was added and the solvent was removed by evaporation. The residue was partitioned between DCM and water. The organic phase was dried (MgSO4), filtered and evaporated to yield an orange oil (1.030 g, 90%).

Provenance & Evidence