Reaction #2069957

Reaction equation

Phosphorus oxychloride

compound

N-[2-Hydroxy-2-(3-methoxyphenyl)ethyl]-2-(4-butylphenyl)-acetamide

sodium hydrogencarbonate

→

title compound

Yield 15.8%

1-(4-Butylbenzyl)-6-methoxyisoquinoline

Yield 15.8%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureunder reflux for 1 hour 30 minutes
2. 2
   TemperatureThe mixture was cooled on ice
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was purified by silica gel column chromatography

Procedure

Phosphorus oxychloride (1.6 ml) was added to a solution of the compound of Example B145 (600 mg, 1.7 mmol) in acetonitrile (15 ml), and the mixture was stirred under reflux for 1 hour 30 minutes. The mixture was cooled on ice, made alkaline with a 5% aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (82 mg).

Source