Hydrazine hydrate (1:1) → 4-Methoxy-3-(4-methylpiperazin-1-yl)aniline

HRID 1708057Notes

Reaction equation

HRID 1708057 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[O:17][CH3:18])[CH2:4][CH2:3]1.O.NN>C(O)C.[Ni].O>[CH3:18][O:17][C:9]1[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:8]=1[N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 104448521-(2-Methoxy-5-nitrophenyl)-4-methylpiperazine

Product 1

HCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)anilineYield 53%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of step (a) (5.07 g) in ethanol (70 ml) was added a paste of Raney Nickel in water (2 g). To the warmed suspension was added, with constant agitation, hydrazine hydrate (5 ml) dropwise during 20 min with occasional warming. After the main effervescence had ceased, the suspension was heated for 15 min and then filtered with the aid of ethanol under nitrogen. The residues were kept moist and washed with ethanol and the combined filtrate and washings were evaporated to dryness with the aid of ethanol. The dark residue was re-evaporated with ethanol (20 ml), resuspended in ether (40 ml) and the mixture filtered. The residue was washed with ether and dried to give a solid consisting of the title compound (2.365 g)

Workup

  1. temperaturethe suspension was heated for 15 min
  2. filtrationfiltered with the aid of ethanol under nitrogen
  3. washwashed with ethanol
  4. customthe combined filtrate and washings were evaporated to dryness with the aid of ethanol
  5. customThe dark residue was re-evaporated with ethanol (20 ml)
  6. filtrationthe mixture filtered
  7. washThe residue was washed with ether
  8. customdried
  9. customto give a solid

Sources & evidence

ORD record
ord-d81267578e2f495a9abe2d308b8be1d7
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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