Acetonitrile → HCID 69648825, compound

HRID 1744510Notes

Reaction equation

HRID 1744510 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].[CH3:13][C@H:14]1[CH2:19][NH:18][CH2:17][C@@H:16]([CH3:20])[NH:15]1.C(#N)C>O>[CH3:13][C@H:14]1[NH:15][C@@H:16]([CH3:20])[CH2:17][N:18]([C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[C:4]#[N:5])[CH2:19]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 855042-Chloro-5-nitrobenzonitrileHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 69648825HCID 69648825, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-5-nitrobenzonitrile (13.3 g) and cis-2,6-dimethylpiperazine (25 g) were added to acetonitrile (25 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was added to water and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether to give cis-2-(3,5-dimethylpiperazin-1-yl)-5-nitrobenzonitrile (14.3 g), melting point: 109–110° C.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-d3794dc1ed6447839b1ceb9554fc154c
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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