Potassium Carbonate → 1-(5-Chloro-2-nitrophenyl)-4-methylpiperazine

HRID 1292988Notes

Reaction equation

HRID 1292988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 28296181-(5-Chloro-2-nitrophenyl)-4-methylpiperazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-fluoro-nitrobenzene (28.5 mmol), 1-methylpiperazine (28.5 mmol) and K2CO3 (37.0 mmol) in DMF is stirred at 100° C. for 16 h and diluted with water and EtOAc. The phases are separated and the aqueous phase is extracted with EtOAc. The organic phase and the extracts are combined, washed sequentially with water and brine, dried over Na2SO4 and dried in vacuo. The resultant residue is chromatographed (silica gel, 10% methanol in EtOAc as eluent) to afford the title product.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with EtOAc
  3. washwashed sequentially with water and brine
  4. dry with materialdried over Na2SO4
  5. customdried in vacuo
  6. customThe resultant residue is chromatographed (silica gel, 10% methanol in EtOAc as eluent)

Sources & evidence

ORD record
ord-3eaad978cd204cc088f9ef21a83d5b1e
Source dataset
uspto-grants-2007_07
Patent number
US07238696B2

Reaction notes

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