Water → 5-Nitro-2-(1-piperazinyl)benzonitrile

HRID 2184855Notes

Reaction equation

HRID 2184855 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.O>COCCO>[C:4]([C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 167682915-Nitro-2-(1-piperazinyl)benzonitrileYield 99.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-5-nitrobenzonitrile (1 g) and piperazine (2.12 g) in ethylene glycol monomethyl ether (5 mL) was heated at 60° C. for 30 minutes. After cooling to room temperature, H2O was added (50 mL) and the solution extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with H2O, dried over Na2SO4 and evaporated to dryness to give 1.27 g (99%) of the desired compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe solution extracted with CH2Cl2 (3×25 mL)
  3. washThe combined organic layers were washed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5cc7a83edf3c40e59f8afa3cba7e7001
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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