Ethanol → 5-Nitro-2-(2-hydroxyethylpiperazin-1-yl)benzonitrile

HRID 1744499Notes

Reaction equation

HRID 1744499 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].[N:13]1(C(O)C)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[CH2:22]([OH:24])[CH3:23]>>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][OH:24])=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 855042-Chloro-5-nitrobenzonitrileHCID 177695631-(Piperazin-1-yl)ethan-1-ol

Product 1

HCID 222281915-Nitro-2-(2-hydroxyethylpiperazin-1-yl)benzonitrile

Procedure

2-Chloro-5-nitrobenzonitrile (15 g) and piperazinoethanol (16 g) were added to ethanol (100 ml) and the mixture was stirred at a refluxing temperature for 1 h. The solvent was evaporated under reduced pressure. To the residue was added aqueous sodium hydroxide solution and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. To the residue diisopropyl ether was added to allow crystallization. The crystals were recrystallized from hydrous ethanol to give 5-nitro-2-(2-hydroxyethylpiperazin-1-yl)benzonitrile (18.7 g), melting point 100–102° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionTo the residue was added aqueous sodium hydroxide solution
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. additionTo the residue diisopropyl ether was added
  8. customcrystallization
  9. customThe crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-e9fb11f7b6aa4ae392142ff81f74b351
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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