Reaction #79138

Reaction equation

water

6-(Bromoacetyl)-5-fluoro-3,4-dihydro-2(1H)-quinolinone

triethylamine

4-(3-Methoxyphenyl)-4-piperidinol

→

5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one

Yield 28.2%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Filtrationthe resulting precipitate was filtered

Procedure

To a cooled solution of 6-(Bromoacetyl)-5-fluoro-3,4-dihydro-2(1H)-quinolinone (900 mg, 3.1 mmol) and triethylamine (0.88 ml, 6.3 mmol) in DMF (15 ml) was added dropwise a solution of 4-(3-Methoxyphenyl)-4-piperidinol (650 mg, 3.1 mmol) in DMF(15 ml) at 0° C. The mixture was stirred at room temperature for 3 h. The reaction mixture was added water and the resulting precipitate was filtered to afford 5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one (360 mg) as a brown solid. The filtrate was extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (dichloromethane/methanol=20/1) to afford 5-Fluoro-6-[[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]acetyl]-3,4-dihydroquinolin-2(1H)-one as a yellow solid (270 mg). The obtained products were combined and used in the next step without further purification.

Source