Hydrazine hydrate (1:1) → HCID 59850188, compound

HRID 2064156Notes

Reaction equation

HRID 2064156 reaction equation
[Cl: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]>[Cl: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 59850194HCID 59850194, compound

Product 1

HCID 59850188HCID 59850188, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

N-(5-Chloro-4-trifluoromethyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D51) (0.64 g, 1.57 mmole) was dissolved in ethanol (25 ml) and Raney nickel (50% aqueous suspension, 100 mg) was added at room temperature; the mixture was heated to 60° C. and hydrazine monohydrate (0.8 ml) was added over 30 min. After 2 hr more, the reaction mixture was cooled to room temperature, filtered through Celite and the solvent was evaporated to dryness. The residue was purified by silica gel chromatography eluting with 2 to 20% methanol in dichloromethane to yield the title compound as a cream solid, 0.34 g, 58%. MH+=378 and 380.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customthe solvent was evaporated to dryness
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 2 to 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-548078dd40644f05bd8d6c5a44022dc3
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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