3-[[4-(4-Nitrophenyl)-1-piperazinyl]methyl]benzonitrile → 4-[4-(3-Cyano-benzyl)-piperazin-1-yl]-phenylamine

HRID 1267112Notes

Reaction equation

HRID 1267112 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2]>CCO.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2]

Participants

4

Reactant 1

HCID 85908193-[[4-(4-Nitrophenyl)-1-piperazinyl]methyl]benzonitrile

Product 1

HCID 111854474-[4-(3-Cyano-benzyl)-piperazin-1-yl]-phenylamineYield 85.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 1-(3-cyano-benzyl)-4-(4-nitro-phenyl)-piperazine (52 g) in EtOH (1.2 L) and THF (300 mL) was added portionwise SnC2.2H2O (145.6 g) at room temperature and the mixture was heated at 55° C. for 16 hours. After evaporation of the solvents, the residue was taken in water, basified with NaOH at pH 14 and extracted with CH2Cl2. The organic layer was then washed with water, dried over Na2SO4, and evaporated. The residue was cristallized from disopropyl ether to give the title compound (40.5 g) as pale yellow crystals.

Workup

  1. customAfter evaporation of the solvents
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was then washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ac384ac2747045f3a8ff3879b7ffcecf
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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