Ammonia → 1-(4-Aminophenyl)piperazin-2-one

HRID 18540Notes

Reaction equation

HRID 18540 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)([O-])=O.N.[H][H]>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]2=[O:16])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 23086769HCID 23086769, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 534061751-(4-Aminophenyl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 670 mg 1-(4-Nitro-phenyl)-1H-pyrazin-2-one in 100 mL MeOH, 8 g Raney Nickel (washed three times with MeOH) were introduced under a nitrogen atmosphere. Then 10 mL of a 7 M solution of NH3 in MeOH were added. The nitrogen atmosphere was replaced by a hydrogen atmosphere and the mixture was hydrogenated under normal pressure at RT. After 2 h the reaction mixture was filtered through a pad of celite. The solvents were removed under reduced pressure and the residue was subjected to the next reaction step without further purification.

Workup

  1. customwas hydrogenated under normal pressure at RT
  2. filtrationAfter 2 h the reaction mixture was filtered through a pad of celite
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-c83c3cd7ec4f44a284775955b7ce9cbc
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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