Water → tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate

HRID 57556Notes

Reaction equation

HRID 57556 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[F:30].O>CN(C=O)C>[F:30][C:22]1[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16203508tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl piperazine-1-carboxylate (1120 mg, 6 mmol) in DMF (25 mL) was added K2CO3 (828 mg, 6 mmol) and 1,2-difluoro-4-nitrobenzene (795 mg, 5 mmol) at room temperature. The reaction was stirred at 80° C. for 24 hours. After that, the reaction was poured into 50 mL of water and extracted with EA (3×25 mL), washed with H2O (25 mL) and brine (25 mL), dried over Na2SO4 and concentrated to give yellow solid. MS (m/z): 226 (M−99)+

Workup

  1. extractionextracted with EA (3×25 mL)
  2. washwashed with H2O (25 mL) and brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give yellow solid

Sources & evidence

ORD record
ord-6887a601b8754e1a9c97c2337c0ce88c
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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