Potassium Carbonate → 2-(4-Isopropylpiperazin-1-yl)-5-nitrobenzonitrile

HRID 633449Notes

Reaction equation

HRID 633449 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:13]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[C:4]#[N:5])[CH2:18][CH2:17]1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 339954542-(4-Isopropylpiperazin-1-yl)-5-nitrobenzonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-5-nitrobenzonitrile (1.08 g, 6.50 mmol, 1 equiv), 1-isopropylpiperazine (1.0 g, 7.80 mmol, 1.2 equiv), and K2CO3 (2.69 g, 19.50 mmol, 3 equiv) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between excess water and EtOAc, and then the layers were separated. The aqueous layer was extracted with EtOAc 2×, and the combined organic layer was washed with brine 1×. The organic layer was dried over Na2SO4, filtered, and concentrated to dryness to provide 2-(4-isopropylpiperazin-1-yl)-5-nitrobenzonitrile (1.76 g, 99% yield) as a brown oil that was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between excess water and EtOAc
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc 2×
  4. washthe combined organic layer was washed with brine 1×
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-30c52d4c6ec54ae1af697a1ae8c3f31f
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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