Hydrazine hydrate (1:1) → HCID 59850151, compound

HRID 2064149Notes

Reaction equation

HRID 2064149 reaction equation
[F:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[C:4]([N+:23]([O-])=O)[CH:3]=1.O.NN>C(O)C.[Ni]>[NH2:23][C:4]1[CH:3]=[C:2]([F:1])[C:7]([Br:8])=[CH:6][C:5]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59850185HCID 59850185, compound

Product 1

HCID 59850151HCID 59850151, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

1,1-Dimethylethyl 4-[(4-fluoro5-bromo-2-nitrophenyl)amino]-piperidinecarboxylate (D43) (0.91 g, 2.2 mmole) was suspended in ethanol (25 ml) and Raney nickel (50% aqueous suspension, 100 mg) was added at room temperature; the mixture was heated to 45° C. and hydrazine monohydrate (3.0 ml) was added over 10 min. After 1 hr more, the reaction mixture was cooled to room temperature, filtered through Celite and the solvent was evaporated to yield the title compound as an orange brown gum, 0.83 g, 98%. LC/MS—96% m/e 388/390 (M+H).

Workup

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

Sources & evidence

ORD record
ord-86778ee9b8fe4fcc8751bbb30d87a4e6
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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