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Methyl iodide → (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(N-methyl-1H-indol-3-yl-methyl)piperazine

HRID 1418560
ノート
印刷プレビュー

反応式

HRID 1418560 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C@H:10]([CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:42]I>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:16]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:18]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:20]=2)[C@H:10]([CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH3:42])[CH:32]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54406912(2R)-4-benzyl-1-[3,5-bis(trifluoro-methyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine

生成物 1

HCID 86751290(2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(N-methyl-1H-indol-3-yl-methyl)piperazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To an ice-cooled solution of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (1.15 g) in dimethylformamide (60 ml) was added 60% sodium hydride (0.1 g) under nitrogen atmosphere, and the mixture was stirred for 5 minutes. After addition of methyl iodide (0.13 ml), the reaction mixture was stirred for 40 minutes. The reaction was quenched with 0.5N hydrochloric acid (60 ml) and diluted with dichloromethane (80 ml). The organic layer was washed with water, aqueous sodium bicarbonate solution and brine, and dried over magnesium sulfate. After removal of the solvent, the residue was purified on a silica gel column eluting with a mixture of toluene and ethyl acetate (10:1) to give (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(N-methyl-1H-indol-3-yl-methyl)piperazine (1.12 g) as a syrup.

後処理

  1. stirringthe reaction mixture was stirred for 40 minutes
  2. customThe reaction was quenched with 0.5N hydrochloric acid (60 ml)
  3. additiondiluted with dichloromethane (80 ml)
  4. washThe organic layer was washed with water, aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent
  7. customthe residue was purified on a silica gel column
  8. washeluting with a mixture of toluene and ethyl acetate (10:1)

出典と根拠

ORDレコード
ord-a0051df81dc740ff846ed46deb95370e
出典データセット
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05883098

反応ノート

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