Hydrazine hydrate (1:1) → HCID 59850187, compound

HRID 2064159Notes

Reaction equation

HRID 2064159 reaction equation
[Br:1][C:2]1[C:3]([C:24]([F:27])([F:26])[F:25])=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:7]=1.O.NN>C(O)C.[Ni]>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:13][CH2:14]2)[C:5]([NH2:21])=[CH:4][C:3]=1[C:24]([F:26])([F:25])[F:27]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59850135HCID 59850135, compound

Product 1

HCID 59850187HCID 59850187, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A stirred suspension of N-[5-bromo-2-nitro-4-(trifluoromethyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D54) (380 mg, 0.84 mmole) in ethanol (20 ml) at room temperature under argon was treated with Raney Nickel (20 mg) followed by the dropwise addition of hydrazine hydrate (0.25 ml, 8.0 mmole). The mixture was maintained at room temp. for 0.5 hr, then heated at 45° C. for 1 hr producing a grey solution, which was filtered through Kieselguhr and the filtrate concentrated under vacuum to afford the title compound as a pale yellow solid (350 mg, 99%). MH+=422, 424.

Workup

  1. temperatureThe mixture was maintained at room temp. for 0.5 hr
  2. customproducing a grey solution, which
  3. filtrationwas filtered through Kieselguhr
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-1ab1cafc6abd4e968ac2245e275613b6
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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