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

HRID 2064153Notes

Reaction equation

HRID 2064153 reaction equation
[CH3:1][O:2][C:3]1[C:4]([Cl:26])=[CH:5][C:6]([N+:23]([O-])=O)=[C:7]([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)[CH:8]=1.O.NN>C(O)C.[Ni]>[NH2:23][C:6]1[CH:5]=[C:4]([Cl:26])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 598501431,1-Dimethylethyl 4-[(5-methoxy-4-chloro-2-nitrophenyl)amino]-piperidinecarboxylate

Product 1

HCID 598502131,1-Dimethylethyl 4-[(2-amino-4-chloro-5-methoxyphenyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

1,1-Dimethylethyl 4-[(5-methoxy-4-chloro-2-nitrophenyl)amino]-piperidinecarboxylate (D47) (400 mg) was dissolved in ethanol (10 ml) and Raney nickel (50% aqueous suspension, 1.0 ml) was added at room temperature; the mixture was heated to 40° C. and hydrazine monohydrate (0.5 ml) was added over 30 min. After 30 min more, the reaction mixture was cooled to room temperature, filtered through Celite evaporated and chromatographed on silica gel eluting with ethyl acetate-hexane mixtures to yield the title compound, 300 mg.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customevaporated
  4. customchromatographed on silica gel eluting with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-757b8a5e1d1d488b936178e4f44e59fa
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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