Hydrazine hydrate (1:1) → HCID 59850166, compound

HRID 2064121Notes

Reaction equation

HRID 2064121 reaction equation
[Cl:1][C:2]1[C:3]([F:25])=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.O.NN>C(O)C.[Ni]>[NH2:22][C:5]1[CH:4]=[C:3]([F:25])[C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59850148HCID 59850148, compound

Product 1

HCID 59850166HCID 59850166, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

1,1-Dimethylethyl 4-[(5-chloro-4-fluoro-2-nitrophenyl)amino]-piperidinecarboxylate (D2) (0.91 mmol, 340 mg) was dissolved in ethanol (20 ml) and an aqueous suspension of Raney-Nickel (1 ml) was added at room temperature; the mixture was heated to 40° C. and hydrazine monohydrate (15 eq., 13.7 mmol, 0.424 ml) was added over 20 min at 40° C. The reaction mixture was then cooled to room temperature, filtered through celite and the solvent was evaporated to yield the title compound, which was purified by chromatography, complete conversion, 312 mg, M+−H=342.

Workup

  1. additionwas added at room temperature
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered through celite
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-657840b3ac7a40399bc4cf06fc13e150
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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