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

HRID 227300Notes

Reaction equation

HRID 227300 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-a730efe6c8eb4414844be7365e25ce56
Source dataset
uspto-grants-2009_07
Patent number
US07560470B2

Reaction notes

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