4-(cis-3,5-Dimethyl-1-piperazinyl)-2-nitrobenzonitrile → 2-Amino-4-(cis-3,5-dimethyl-1-piperazinyl)benzonitrile

HRID 130416Notes

Reaction equation

HRID 130416 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([N+:17]([O-])=O)[CH:10]=2)[CH2:3]1>C(O)C.CO.[Pd]>[NH2:17][C:11]1[CH:10]=[C:9]([N:4]2[CH2:5][C@H:6]([CH3:8])[NH:7][C@H:2]([CH3:1])[CH2:3]2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

5

Reactant 1

HCID 691981564-(cis-3,5-Dimethyl-1-piperazinyl)-2-nitrobenzonitrile

Product 1

HCID 590070532-Amino-4-(cis-3,5-dimethyl-1-piperazinyl)benzonitrile

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of the product of Step 1 (186 mg, 0.71 mmol) in ethanol (14 ml) and methanol (3-4 ml) was treated with palladium on charcoal (37 mg, 10% paste) and stirred under an atmosphere of hydrogen for 16 hours. The mixture was then filtered through celite, washing with ethanol and the then evaporated in vacuo. Purification of the residue by mass directed autoprep HPLC gave the title compound (D20) as the formic acid salt. MS (ES+) m/e 231 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with ethanol
  3. customthe then evaporated in vacuo
  4. customPurification of the residue by mass

Sources & evidence

ORD record
ord-62f2dbcac9c041e1a1fe36a4b5ded636
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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