1,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one → 3-[(N-Benzyl-piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

HRID 1681991ノート

反応式

HRID 1681991 の反応式
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.CC(C)([O-])C.[K+].[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH2:36]Br)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CS(C)=O>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH2:36][N:9]2[C:8](=[O:12])[CH2:7][C:6]3[CH:13]=[C:14]([O:15][CH3:16])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH:11]=[CH:10]2)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 190759011-Benzyl-3-(bromomethyl)piperidineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 198035973-[(N-Benzyl-piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

17.54 g (0.08 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one are suspended in 150 ml of dimethylsulphoxide and 8.98 g (0.08 mol) of potassium tert.butoxide are added with stirring. After 45 minutes, 21.45 g (0.08 mol) of N-benzyl-3-(bromomethyl)-piperidine dissolved in 50 ml of dimethylsulphoxide are added dropwize to the resulting solution with stirring. After 2 hours the mixture is poured onto ice water. The aqueous phase is extracted three times, each time with 150 ml of ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulphate, concentrated by evaporation in vacuo and purified over 800 g of aluminium oxide (neutral, activity II-III) with methylene chloride and then with increasing amounts of ethanol (up to 3%). Yield: 14.3 g (44% of theory), Rf value: 0.35 (aluminium oxide neutral, eluant: 1% ethanol in methylene chloride).

後処理

  1. additionare added dropwize to the resulting solution
  2. stirringwith stirring
  3. additionAfter 2 hours the mixture is poured onto ice water
  4. extractionThe aqueous phase is extracted three times
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation in vacuo
  8. custompurified over 800 g of aluminium oxide (neutral, activity II-III) with methylene chloride

出典と根拠

ORDレコード
ord-bba51b87378f4483b67d67964452067c
出典データセット
uspto-grants-1992_12
特許番号
US05175157

反応ノート

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