Piperazine → HCID 19367121, compound

HRID 1416262Notes

Reaction equation

HRID 1416262 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:9]=1[C:10]#[N:11]>CN(C=O)C>[F:16][C:13]1[CH:14]=[CH:15][C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[C:9]([CH:12]=1)[C:10]#[N:11]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 1235582,5-Difluorobenzonitrile

Product 1

HCID 19367121HCID 19367121, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of piperazine (Aldrich; 1.28 g), 2,5-difluorobenzonitrile (Lancaster; 0.422 g), and DMF (4 mL) is stirred at 80° C. for 1.5 h, after which the mixture is cooled and partitioned between dichloromethane, water, and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate, concentrated, and the residue is crystallized from dichloromethane/ethyl ether/hexane to give 0.282 g of 5-fluoro-2-(piperazin-1-yl)benzonitrile; mp 83-83.5° C.; 1H NMR (CDCl3) δ3.10, 7.00, 7.21, 7.27.

Workup

  1. temperatureafter which the mixture is cooled
  2. custompartitioned between dichloromethane, water, and aq. sodium bicarbonate
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is crystallized from dichloromethane/ethyl ether/hexane

Sources & evidence

ORD record
ord-43a9b9c6af194a7a97bc1e25dd708430
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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