Cesium carbonate → 5-Bromo-2-(4-methyl-piperazin-1-yl)-benzonitrile

HRID 1175171Notes

Reaction equation

HRID 1175171 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 595583365-Bromo-2-(4-methyl-piperazin-1-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Bromo-2-fluorobenzonitrile (2.0 g, 10 mmol), Cesium carbonate (6.58 g, 20 mmol) and 1-methylpiperazine (1.35 ml, 12 mmol) in 100 ml DMSO are stirred at 120 C for 1 hour. The reaction is quenched by the addition of water and extracted with ethyl acetate. The organic phases are dried and the solvent evaporated. The product obtained is considered pure enough for the next synthesis steps. LC-MS (m/z, ES+): 280 (MH+), Retention time: 1.03 mins (LC-MS method 8)

Workup

  1. customThe reaction is quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. customThe organic phases are dried
  4. customthe solvent evaporated
  5. customThe product obtained
  6. customis considered pure enough for the next synthesis steps

Sources & evidence

ORD record
ord-56daa61b81b24ba49faa38c4e0050ab8
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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