Hydrazine hydrate (1:1) → HCID 59850178, compound

HRID 2064171Notes

Reaction equation

HRID 2064171 reaction equation
[Br:1][C:2]1[C:3]([C:25]([F:28])([F:27])[F:26])=[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]([C:25]([F:28])([F:26])[F:27])[C:2]([Br:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59850172HCID 59850172, compound

Product 1

HCID 59850178HCID 59850178, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A stirred suspension of 1,1-dimethylethyl 4-{[5-bromo-2-nitro-4-(trifluoromethyl)phenyl]amino}-1-piperidinecarboxylate (D66, 1.10 g, 2.3 mmol) in ethanol (50 ml) at room temperature under argon was treated with Raney Nickel (30 mg) followed by dropwise addition over 10 minutes of hydrazine hydrate (0.50 ml, 16 mmol). The mixture was stirred well at room temperature for 20 minutes, then heated at 45° C. for 1 hr, before cooling to 20° C. and filtering through Kieselguhr. The filtrate was concentrated under vacuum to afford the title compound as a white solid (0.98 g, 95%).

Workup

  1. temperatureheated at 45° C. for 1 hr
  2. temperaturebefore cooling to 20° C.
  3. filtrationfiltering through Kieselguhr
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-5470bc672a984b41ae3ddc58333ba476
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

Loading…