Réaction #6850

Équation de réaction

Phosphorus oxychloride

N-[2-(4-methoxy-phenyl)-ethyl]-acetamide

→

7-methoxy-1-methyl-3,4-dihydro-isoquinoline

Rendement 45.3%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 mL)
3. 3
   Lavagewashed with aqueous sodium bicarbonate (saturated, 100 mL) and brine (100 mL)
4. 4
   SéchageThe dichloromethane layer was dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated
7. 7
   AutreThe crude product was purified by column chromatography (5% methanol in dichloromethane)

Mode opératoire

Phosphorus oxychloride (22.5 mL) was added to a solution of N-[2-(4-methoxy-phenyl)-ethyl]-acetamide (6.5 g) in acetonitrile (200 mL). The mixture was heated at 120° C. in a sealed tube for 16 h. The solvent was evaporated. The residue was dissolved in dichloromethane (200 mL) and washed with aqueous sodium bicarbonate (saturated, 100 mL) and brine (100 mL). The dichloromethane layer was dried over sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography (5% methanol in dichloromethane) to afford 7-methoxy-1-methyl-3,4-dihydro-isoquinoline (2.67 g).

Source