Tetrahydrofuran → N-(2-methoxyphenyl)-4-(morpholin-4-ylmethyl)benzamide

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.

1. temperaturewith cooling in an ice bath
2. stirringstirring for 2.5 hours at 60° C.
3. extractionextracted with ethyl acetate
4. customAfter removing insoluble materials
5. filtrationby filtration
6. washthe organic layer was washed with water and saturated brine
7. dry with materialdried on anhydrous sodium carbonate
8. customThereafter, the solvent was removed by evaporation
9. customthe resulting residue was purified

ORD record

ord-9314116e4867418e938602e89b4994f8

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728835