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

HRID 1403211

반응식

HRID 1403211 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b5290798333a46dba1f9ed8d4d411303
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912200B2

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