5-(4-Methylpiperazinyl)-2-nitrobenzenecarbonitrile → 2-Amino-5-(4-methyl-1-piperazinyl)benzonitrile

HRID 2377826Notes

Reaction equation

HRID 2377826 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:16]([O-])=O)=[C:12]([C:14]#[N:15])[CH:13]=2)[CH2:4][CH2:3]1>CCOC(C)=O.[Pd]>[NH2:16][C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:13][C:12]=1[C:14]#[N:15]

Participants

4

Reactant 1

HCID 161020595-(4-Methylpiperazinyl)-2-nitrobenzenecarbonitrile

Product 1

HCID 219285192-Amino-5-(4-methyl-1-piperazinyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Methylpiperazinyl)-2-nitrobenzenecarbonitrile (1.0 equivalent) was dissolved in EtOAc. The flask was purged with nitrogen, and 10% Pd/C (0.1 equivalents) was added. The flask was evacuated and purged with H2 three times. The resulting mixture was stirred for three days at room temperature. The mixture was filtered through Celite and the filter pad was washed with EtOAc. The solvent was removed in vacuo to give a yellow solid which was purified by silica gel chromatography (5:1:95 MeOH:Et3N:EtOAc) to give the desired product as a yellow solid. LC/MS m/z 217.3 (MH+), Rt 0.95 minutes.

Workup

  1. additionwas added
  2. customThe flask was evacuated
  3. custompurged with H2 three times
  4. filtrationThe mixture was filtered through Celite
  5. washthe filter pad was washed with EtOAc
  6. customThe solvent was removed in vacuo
  7. customto give a yellow solid which
  8. customwas purified by silica gel chromatography (5:1:95 MeOH:Et3N:EtOAc)

Sources & evidence

ORD record
ord-91eec7c4dafa416fab0faa5ee74ac86e
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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