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

HRID 1403211Notes

Reaction equation

HRID 1403211 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b5290798333a46dba1f9ed8d4d411303
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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