Water → n-(2-Amino-4-((4-phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

HRID 1282070Notes

Reaction equation

HRID 1282070 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[CH:7]=[CH:6][C:5]=1[CH2:23][NH:24][C:25](=[O:27])[CH3:26])([O-])=O.O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)[CH:7]=[CH:6][C:5]=1[CH2:23][NH:24][C:25](=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 18423156N-(2-Nitro-4-((4-phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

Product 1

HCID 18423128n-(2-Amino-4-((4-phenylpiperazin-1-yl)methyl)phenylmethyl)acetamideYield 104.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(2-nitro-4-((4-phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide (0.5 g) and water-containing Raney-nickel (0.5 g) in ethanol (8 ml) was added dropwise hydrazine monohydrate (0.7 ml) and the mixture was refluxed under heating at room temperature for 1 hr. Raney-nickel was removed by passing the mixture through Celite and the solvent was evaporated to give a white solid (0.48 g). The obtained white solid was crystallized from hexane/ethyl acetate (1:1, 100 ml) to give the title compound (45.5 g) as white crystals, m.p.=148-149° C.

Workup

  1. temperaturethe mixture was refluxed
  2. customRaney-nickel was removed
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6a5758f507e94ef6b0058edbc6655780
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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