Piperazine → 4-Fluoro-2-(piperazin-1-yl)benzonitrile

HRID 1416286Notes

Reaction equation

HRID 1416286 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>CN(C)C(=O)C>[C:10]([C:9]1[CH:8]=[CH:15][C:14]([F:16])=[CH:13][C:12]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)#[N:11]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 775452,4-Difluorobenzonitrile

Product 1

HCID 193671084-Fluoro-2-(piperazin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
122 °C

Procedure

A mixture of piperazine (Aldrich; 3.99 g), 2,4-difluorobenzonitrile, and N,N-dimethylacetamide (20 mL) is stirred for 1.5 h at 122° C. After cooling, the mixture is partitioned between dichloromethane and satd. aq. sodium bicarbonate. The organic layers are dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel and the appropriate fractions are combined and concentrated to give 1.44 g of 1-(2-cyano-5-fluorophenyl)piperazine; 1H NMR (CDCl3) δ3.01, 3.30, 6.56, 6.63, 7.40.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between dichloromethane
  3. dry with materialThe organic layers are dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5980976b2f5f4071b3a4e96b7f854466
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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