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

HRID 2064166Notes

Reaction equation

HRID 2064166 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[C:5]([N+:24]([O-])=O)[CH:4]=1.O.NN>C(O)C.[Ni]>[NH2:24][C:5]1[CH:4]=[C:3]([C:2]([F:28])([F:1])[F:27])[C:8]([Cl:9])=[CH:7][C:6]=1[NH:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 598501301,1-Dimethylethyl 4-[(4-trifluoromethyl-5-chloro-2-nitrophenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 598501981,1-Dimethylethyl 4-[(2-amino-5-chloro-4-trifluoromethylphenyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1,1-Dimethylethyl 4-[(4-trifluoromethyl-5-chloro-2-nitrophenyl)amino]-1-piperidinecarboxylate (D61, 6.7 g) was dissolved in ethanol (100 ml) and Raney nickel (50% aqueous suspension, 5 ml) was added at room temperature; the mixture was heated to 50° C. and hydrazine monohydrate (3 ml) was added over 30 min. After 1 h more, the reaction mixture was cooled to room temperature, filtered through Celite, evaporated, re-evaporated from toluene, and the residue crystallised from dichloromethane to yield the subtitle compound, 4.0 g.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customevaporated
  4. customre-evaporated from toluene
  5. customthe residue crystallised from dichloromethane

Sources & evidence

ORD record
ord-694cad49006944a9a59d96ee4d98c722
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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