2-Chloro-1-fluoro-4-nitrobenzene → 1-acetyl-4-(2-chloro-4-nitrophenyl)piperazine

HRID 1441354Notes

Reaction equation

HRID 1441354 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[C:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])[CH3:13]>CCOC(C)=O.O>[C:12]([N:15]1[CH2:20][CH2:19][N:18]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[Cl:1])[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 837951-Acetylpiperazine

Product 1

HCID 28875881-acetyl-4-(2-chloro-4-nitrophenyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-fluoro-4-nitrobenzene (10 g, 57 mmol) and 1-acetylpiperazine (14.6 g, 114 mmol) were heated neat at 55° C. for 1 h. Then the reaction mixture was allowed to cool down to room temperature. The viscous orange solution was diluted with EtOAc and water. The organics were washed with water (3 times), brine, dried and evaporation of the solvent gave an orange oil which was triturated with isohexane. After evaporation of solvent the title compound was obtained as a yellow solid which was dried overnight in vac oven at 50° C. (15.68 g, 97%). It was used without further purification. NMR (400 MHz) 2.03 (d, 3H), 3.18 (dt, 4H), 3.62 (m, 4H), 7.30 (d, 1H), 8.17 (dd, 1H), 8.26 (d, 1H); m/z 284-286.

Workup

  1. washThe organics were washed with water (3 times), brine
  2. customdried
  3. customevaporation of the solvent
  4. customgave an orange oil which
  5. customwas triturated with isohexane
  6. customAfter evaporation of solvent the title compound
  7. customwas obtained as a yellow solid which
  8. customwas dried overnight in vac oven at 50° C. (15.68 g, 97%)
  9. customIt was used without further purification

Sources & evidence

ORD record
ord-b04e436f1cae4cdaa086f793015682a1
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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