Reaction #573778

Reaction equation

N-[4-(4-piperidinyl-carbonyl)phenyl]-acetamide

2-chloro-4'-fluoro-acetophenone

sodium bicarbonate

→

1-(4-Fluorophenyl)-2-[4-[(4-acetamidophenyl)carbonyl]-1-piperidinyl]-ethanone

Solvents

water

tetrahydrofuran

brine

Conditions

Workup

1. 1
   TemperatureThis mixture was heated
2. 2
   Temperatureto reflux for 1.5 hours
3. 3
   Extractionextracted with chloroform
4. 4
   DryingThe organic layer was dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Otherto yield a solid which
8. 8
   Otherwas recrystallized from 2-butanone/cyclohexane

Procedure

To a solution of 3.0g (12.2 mmol) of N-[4-(4-piperidinyl-carbonyl)phenyl]-acetamide in 10 ml of water and 100 ml of tetrahydrofuran was added 2.3 g (13.4 mmol) of 2-chloro-4'-fluoro-acetophenone followed by 2.0g (24.4 mmol) of sodium bicarbonate. This mixture was heated to reflux for 1.5 hours. The reaction mixture was poured into 500 ml of brine and extracted with chloroform. The organic layer was dried with magnesium sulfate, filtered and concentrated to yield a solid which was recrystallized from 2-butanone/cyclohexane. 1-(4-Fluorophenyl)-2-[4-[(4-acetamidophenyl)carbonyl]-1-piperidinyl]-ethanone was obtained as an off-white solid having a mp of 168°-170° C.

Source