HCID 59834622, compound → 1-(4-Ethoxy-2-fluorophenyl)piperazine

HRID 271567Notes

Reaction equation

HRID 271567 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[C:6]([F:23])[CH:5]=1)[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[C:6]([F:23])[CH:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 59834622HCID 59834622, compound

Product 1

HCID 179682601-(4-Ethoxy-2-fluorophenyl)piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-(4-Ethoxy-2-fluoro-phenyl)-piperazine-1-carboxylic acid, tert.-butyl ester (12 mmol) in CH2Cl2 (150 ml), TFA (29 ml) is added at 0° C. The reaction mixture is stirred at room temperature for 1 h. The solvent is removed by evaporation and dried to give crude product, 1-(4-ethoxy-2-fluoro-phenyl)-piperazine. To the crude product in DMF (50 ml), potassium carbonate (30 mmol) is successively added at 0° C. The mixture is stirred at 0° C. for 15 min. 6-Bromomethyl-7-(2,2-dimethyl-propyl)-7.H.-pyrrolo[2,3-.d.]pyrimidine-2-carbonitrile (12 mmol) is added to the mixture at 0° C. The reaction mixture is stirred at room temperature for 3 h and quenched with saturated ammonium chloride. The mixture is extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over magnesium sulfate. The solvent is evaporated and the residue is purified by column chromatography on silica gel using n-hexane:AcOEt=2:1 (v/v).

Workup

  1. customThe solvent is removed by evaporation
  2. customdried

Sources & evidence

ORD record
ord-42f4d40e2208471786933441a084c523
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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