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

HRID 2453

反応式

HRID 2453 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9314116e4867418e938602e89b4994f8
出典データセット
uspto-grants-1998_03
特許番号
US05728835

関連ノート

読み込み中…