Ethyl Acetate → HCID 58824121, compound

HRID 459810Notes

Reaction equation

HRID 459810 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([N+:22]([O-])=O)[C:15]=2[C:25]#[N:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.NN>C(O)C.[Ni].O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([NH2:22])[C:15]=2[C:25]#[N:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 9321HydrazineHCID 58824138HCID 58824138, compound

Product 1

HCID 58824121HCID 58824121, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 370 mg (1.02 mmol) of 4-(2-cyano-5-methoxy-3-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester dissolved in 5 mL ethanol and 5 mL ethyl acetate was added a pipet of Raney nickel slurry in water followed by 64 μL (2 eq., 2.04 mmol) hydrazine. The mixture was stirred 30 minutes to completion, filtered through Celite and concentrated under reduced pressure to provide 300 mg of crude 4-(3-amino-2-cyano-5-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2450851e7b2944578446b55632c4b334
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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