Hydrazine → HCID 66863203, compound

HRID 1985639Notes

Reaction equation

HRID 1985639 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.NN>[Ni]>[NH2:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:18])[CH2:15][CH2:16]2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66863894HCID 66863894, compound

Product 1

HCID 66863203HCID 66863203, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a mixture of [4-(3-amino-4-nitrophenyl)piperazin-1-yl](2-trifluoromethylphenyl)methanone (2.000 g, 5.070 mmol) and Raney Ni (0.5 mL) was added hydrazine (3 mL). The mixture was allowed to stir at room temperature for 5 h. The mixture was then filtered through celite, washed with ethyl acetate. The organic extracts were combined, washed with water and brine, concentrated, and purified by column chromatography to obtain the title compound in 88% yield (1.830 g). 1H NMR (300 MHz, CDCl3) 7.70 (d, 1H, J=7.7 Hz), 7.59 (t, 1H, J=7.3 Hz), 7.50 (t, 1H, J=7.4 Hz), 7.33 (d, 1H, J=7.5 Hz), 6.61 (d, 1H, J=8.3 Hz), 6.34 (d, 1H, J=2.5 Hz), 6.28 (dd, 1H, J=2.6, 8.3 Hz), 3.92 (dd, 1H, J=3.4, 6.1 Hz), 3.28 (t, 1H, J=5.1 Hz), 3.12-3.02 (m, 2H), 2.94-2.80 (m, 2H). MS (ES+) m/z 365.2 (M+1).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashed with ethyl acetate
  3. washwashed with water and brine
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-ec994224c05045ce91c1becda93b6495
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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