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

HRID 2453

반응식

HRID 2453 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([Li])CCC.Cl[CH2:13][C:14]1[CH:30]=[CH:29][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])=[O:19])=[CH:16][CH:15]=1.C1COCC1>CCOCC.O>[CH3:28][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:30][CH:29]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamideHCID 178418339Butyllithium

생성물 1

HCID 869146N-(2-methoxyphenyl)-4-(morpholin-4-ylmethyl)benzamide수율 39.2%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9314116e4867418e938602e89b4994f8
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728835

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