Hydrazine hydrate (1:1) → HCID 59850204, compound

HRID 2064145Notes

Reaction equation

HRID 2064145 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[C:4]([N+:22]([O-])=O)[CH:3]=1.O.NN>C(O)C.[Ni]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH2:12][CH2:11]2)=[C:4]([NH2:22])[CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59850157HCID 59850157, compound

Product 1

HCID 59850204HCID 59850204, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

N-(4,5-Dichloro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D38) (320 mg) was dissolved in ethanol (20 ml) and Raney nickel (50% aqueous suspension, 0.5 ml) was added at room temperature; the mixture was heated to 40° C. and hydrazine monohydrate (0.4 ml) was added over 20 min. After 30 min more, the reaction mixture was cooled to room temperature, filtered through Celite and the solvent was evaporated. Chromatography on silica gel eluting with methanol-dichloromethane mixtures yielded the title compound, 150 mg.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-90048cde4a35424cb99ba4294242e443
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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