Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-[(2-amino-3-fluoro-5-methoxyphenyl)amino]-1-piperidinecarboxylate

HRID 2061477Notes

Reaction equation

HRID 2061477 reaction equation
[N+:1]([C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:5]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:5]=1[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 596832591,1-Dimethylethyl 4-[(2-nitro-3-fluoro-5-methoxyphenyl)amino]-piperidinecarboxylate

Product 1

HCID 596832781,1-Dimethylethyl 4-[(2-amino-3-fluoro-5-methoxyphenyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

1,1-Dimethylethyl 4-[(2-nitro-3-fluoro-5-methoxyphenyl)amino]-piperidine-carboxylate (D12) (380 mg, 1 mmol) was dissolved in ethanol (10 ml) and Raney nickel (50% aqueous suspension, 1 ml) was added at room temperature; the mixture was heated to 40° C. and hydrazine monohydrate (0.5 ml) was added over dropwise. After 30 min more, the reaction mixture was cooled to room temperature, filtered through Celite and the solvent evaporated. The product was purified by silica gel chromatography eluting with 20 to 50% ethyl acetate in hexane to yield the title compound, 250 mg. M+−H=340.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customthe solvent evaporated
  4. customThe product was purified by silica gel chromatography
  5. washeluting with 20 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d2835c65d237420db547594403b03853
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

Loading…