Reaktion #2549

Reaktionsgleichung

THF

n-butyl lithium

morpholine

4-chloromethyl-N-(2-methoxyphenyl)benzamide

→

title compound

Ausbeute 39.2%

N-(2-Methoxyphenyl)-4-morpholinomethylbenzamide

Ausbeute 39.2%

Lösungsmittel

water

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling in an ice bath
2. 2
   workup.STIRRINGstirring for 2.5 hours at 60° C.
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   SonstigeAfter removing insoluble materials
5. 5
   Filtrationby filtration
6. 6
   Waschenthe organic layer was washed with water and saturated brine
7. 7
   Trocknendried on anhydrous sodium carbonate
8. 8
   SonstigeThereafter, the solvent was removed by evaporation
9. 9
   Sonstigethe resulting residue was purified

Vorschrift

In an atmosphere of argon, morpholine (192 mg, 2.2 mmol) was dissolved in ether (5 ml) to which, with cooling in an ice bath, was subsequently added n-butyl lithium (1.45 ml, 1.52M, 2.2 mmol). After 5 minutes of stirring at room temperature, to this was added 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) at the same temperature. After adding THF (5 ml) and stirring for 2.5 hours at 60° C., the reaction solution was mixed with water (20 ml) and extracted with ethyl acetate. After removing insoluble materials by filtration, the organic layer was washed with water and saturated brine and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether) to obtain 128 mg (39.2%) of the title compound in the form of light yellow solid.

Quelle