1-Methylpiperazine → 1-(2-Fluoro-4-iodobenzyl)-4-methylpiperazine

HRID 56075Notes

Reaction equation

HRID 56075 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C1C(=O)N(Br)C(=O)C1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)(Cl)(Cl)Cl.CCO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:22]1[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 67184N-bromobutanimideHCID 1234922-Fluoro-4-iodotoluene

Product 1

HCID 900224931-(2-Fluoro-4-iodobenzyl)-4-methylpiperazineYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 2-fluoro-4-iodotoluene (0.94 g, 4.0 mmol) in CCl4 (40 mL) were added BPO (0.02 g, 0.08 mmol) and NBS (0.78 g, 4.4 mmol) under N2. The reaction mixture was refluxed for 5 h, then cooled and concentrated in vacuo. To the residue was added a solution of methylpiperazine (2.00 g, 20 mmol) in EtOH (40 mL) under N2. The mixture was stirred at rt overnight and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as a white solid (0.69 g, 52%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

Sources & evidence

ORD record
ord-428793b57f3d4fd5afd3cd5b3fa039f4
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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