Hexane → 1-Benzyl-4-(3,4-dimethoxyphenyl)piperidin-4-ol

HRID 1272277ノート

反応式

HRID 1272277 の反応式
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1.[CH2:23]([N:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.O>[CH2:23]([N:30]1[CH2:35][CH2:34][C:33]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)([OH:36])[CH2:32][CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 192201-Benzyl-4-piperidoneHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 178418339Butyllithium

生成物 1

HCID 135355651-Benzyl-4-(3,4-dimethoxyphenyl)piperidin-4-ol収率 71%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of n-butyllithium in hexane (1.56 M, 93.0 mL, 145 mmol) was added dropwise a solution of 4-bromo-1,2-dimethoxybenzene (34.4 g, 158 mmol) in THF (350 ml) under −70° C. and stirred for 30 minutes under argon atmosphere. A solution of 1-benzyl piperidin-4-one (25.0 g, 132 mmol) in THF (50 ml) was added dropwise to the reaction mixture under −60° C., and the mixture was allowed to warm to 0° C. and stirred under ice cooling for 30 minutes. The reaction mixture was diluted with water, concentrated under reduced pressure, and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography and the obtained crystals were washed with hexane to obtain 26.6 g (yield 71%) of the title compound. mp. 112–114° C.

後処理

  1. stirringstirred under ice cooling for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified
  9. washthe obtained crystals were washed with hexane

出典と根拠

ORDレコード
ord-a784dea104e5474d870d832e022c9a72
出典データセット
uspto-grants-2007_04
特許番号
US07208495B2

反応ノート

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