p-Toluenesulfonic acid monohydrate → N-[3-(3,5-dimethoxy-4-hydroxyphenyl) 2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine

HRID 652968ノート

反応式

HRID 652968 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][O:31][CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:24][CH2:23]2)=[O:21])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[O:9]COCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][O:31][CH:32]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:24][CH2:23]2)=[O:21])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[OH:9]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53774023N-[3-[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine

生成物 1

HCID 54135289N-[3-(3,5-dimethoxy-4-hydroxyphenyl) 2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine収率 84.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 270 mg (0.45 mmol) of the amide compound in 5 ml of methanol was added 95 mg (0.5 mmol) of p-toluen esulfonic acid monohydrate,,and the mixture was heated and refluxed for 1 hour under argon atmosphere. The reaction mixture was concentrated by evaporation under reduced pressure, a saturated aqueous solution of sodium hydrcgencarbonate was added to the residue, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected tc silica gel column chromatography, eluted with chlcroform - methanol, to give 200 mg (0.38 mmol) of N-[3-(3,5-dimethoxy-4-hydroxyphenyl) 2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine. Spectrophotometric data of the product support the structure shown below. ##STR93##

後処理

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 1 hour under argon atmosphere
  3. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  4. additiona saturated aqueous solution of sodium hydrcgencarbonate was added to the residue
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. washeluted with chlcroform - methanol

出典と根拠

ORDレコード
ord-5928e1ed38bc4e4fbf1e52e79216ebf8
出典データセット
uspto-grants-1987_06
特許番号
US04673684

反応ノート

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