Hydrazine hydrate (1:1) → 4-Methoxy-3-(4-methylpiperazin-1-yl)aniline
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]1Participants
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
- temperaturethe suspension was heated for 15 min
- filtrationfiltered with the aid of ethanol under nitrogen
- washwashed with ethanol
- customthe combined filtrate and washings were evaporated to dryness with the aid of ethanol
- customThe dark residue was re-evaporated with ethanol (20 ml)
- filtrationthe mixture filtered
- washThe residue was washed with ether
- customdried
- customto give a solid
Sources & evidence
- ORD record
- ord-80b2866a04034eb6a15a1b9a8aa321c5
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05358948
Reaction notes
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