Piperazine → HCID 19367121, compound

HRID 849486Notes

Reaction equation

HRID 849486 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 (4mL) 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) δ 3.10, 7.00, 7.21, 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-c5224b8940c84a1face05486be02362c
Source dataset
uspto-grants-2000_01
Patent number
US06013654

Reaction notes

Loading…