Trifluoroacetic acid → N-(3-iodo-4-methoxyphenyl)-1-methylpiperidin-4-amine

HRID 1403211

反応式

HRID 1403211 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].[C:11](O)([C:13](F)(F)F)=O.C(O[BH-](O[C:28](=O)[CH3:29])OC(=O)C)(=O)C.[CH3:31][N+:32](C)(C)[CH3:33]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][CH:13]2[CH2:11][CH2:31][N:32]([CH3:33])[CH2:28][CH2:29]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 220545963-Iodo-4-methoxyaniline

生成物 1

HCID 71240893N-(3-iodo-4-methoxyphenyl)-1-methylpiperidin-4-amine収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-iodo-4-methoxyaniline (180 mg, 0723 mmol) in DCM (5 mL) 1-methyl-4-piperidone (0.116 mL, 106 mg, 0.940 mmol), TFA (0.290 mL, 429 mg, 3.760 mmol) and tetramethylammonium triacetoxyborohydride (285 mg, 1.084 mmol) were added in sequence. The reaction is completed in 30 min. The reaction mixture was diluted with DCM, washed with saturated solution of sodium hydrogen carbonate (3×5 mL), brine (3×5 mL), dried over sodium sulfate and the solvent was removed under vacuum. The solid crude so obtained was purified by flash chromatography (EtOAc/TEA 99/1) to afford a beige solid that was crystallized from diethylether to afford the title compound as a whitish solid (197 mg, 79%).

後処理

  1. washwashed with saturated solution of sodium hydrogen carbonate (3×5 mL), brine (3×5 mL)
  2. dry with materialdried over sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customThe solid crude so obtained
  5. customwas purified by flash chromatography (EtOAc/TEA 99/1)
  6. customto afford a beige solid
  7. customthat was crystallized from diethylether

出典と根拠

ORDレコード
ord-b5290798333a46dba1f9ed8d4d411303
出典データセット
uspto-grants-2014_12
特許番号
US08912200B2

関連ノート

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