tert-Butyl piperazine-1-carboxylate → HCID 58824142, compound

HRID 901857Notes

Reaction equation

HRID 901857 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+]([O-])=O)[C:18]=1[C:19]#[N:20])([O-:16])=[O:15].O.C(OCC)(=O)C>CN(C=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:21]2[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[C:18]=2[C:19]#[N:20])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 520718DinitrobenzonitrileHCID 22728543Water ethylacetate

Product 1

HCID 58824142HCID 58824142, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-BOC-piperizine (piperazine-1-carboxylic acid tert-butyl ester, 20.0 g, 107.4 mmol) was added to a solution of 2,6-dinitrobenzonitrile (10.27 7 g, 53.2 mmol) in dry DMF (200 ml). After stirring at 50° C. overnight, the reaction mixture was cooled to room temperature and poured into a mixture of water/ethyl acetate. The organic fraction was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting brown residue was purified by flash chromatography to give 4-(2-cyano-3-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as an orange solid (12.172 g, 69%). MS: (M+H)+ 277.1.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washThe organic fraction was washed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic fraction was concentrated in vacuo
  5. customthe resulting brown residue was purified by flash chromatography

Sources & evidence

ORD record
ord-17d6169b6adb4c1284a755f931ebdcb4
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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