Trifluoroacetic acid → 4-[(2S,5R)-2,5-Dimethylpiperazin-1-yl]-2-fluorobenzonitrile

HRID 1593379Notes

Reaction equation

HRID 1593379 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:14]([CH3:15])[CH2:13][N:12](C(OC(C)(C)C)=O)[C@H:11]([CH3:23])[CH2:10]2)=[CH:5][C:4]=1[F:24])#[N:2].FC(F)(F)C(O)=O>ClCCl>[CH3:15][C@H:14]1[CH2:13][NH:12][C@H:11]([CH3:23])[CH2:10][N:9]1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:24])[CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86601755HCID 86601755, compound

Product 1

HCID 686909784-[(2S,5R)-2,5-Dimethylpiperazin-1-yl]-2-fluorobenzonitrileYield 114.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into 150 ml of dichloromethane was dissolved 15.0 g of tert-butyl (2R,5S)-4-(4-cyano-3-fluorophenyl)-2,5-dimethylpiperazine-1-carboxylate, and then 30 ml of trifluoroacetic acid was added thereto, followed by stirring at room temperature overnight. After the reaction solution was removed by evaporation, 1M hydrochloric acid was added thereto, followed by washing with chloroform. The aqueous phase was made basic with a 5M sodium hydroxide aqueous solution, followed by extraction with chloroform. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by evaporation to obtain 12.0 g of the title compound.

Workup

  1. customAfter the reaction solution was removed by evaporation, 1M hydrochloric acid
  2. additionwas added
  3. washby washing with chloroform
  4. extractionfollowed by extraction with chloroform
  5. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-1623394ed6c54c798a53602a02ab42bb
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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