tert-Butyl piperazine-1-carboxylate → HCID 58824138, compound

HRID 459809Notes

Reaction equation

HRID 459809 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:6]([C:7]#[N:8])=[C:5]([N+:14]([O-])=O)[CH:4]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28]N[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:14]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:6]=2[C:7]#[N:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 15527620HCID 15527620, compound

Product 1

HCID 58824138HCID 58824138, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To 1.32 g (5.92 mmol)of 4-methoxy-2,6-dinitrobenzonitrile dissolved in 8 mL dimethylformamide was added 2.2 g (2 eq., 11.83 mmol) piperazine-1-carboxylic acid tert-butyl ester. The mixture was heated to 50° C. and stirred overnight, then partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography, eluting with ethyl acetate/hexanes provided 1.48 g of 4-(2-cyano-5-methoxy-3-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washColumn chromatography, eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b5b5fcb33b60450d98dcb93c88a36433
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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