Benzene, 1-fluoro-2-methyl-4-nitro- → 1-Acetyl-4-(2-methyl-4-nitrophenyl)piperazine

HRID 1713790

Reaction equation

HRID 1713790 reaction equation
F[P-](F)(F)(F)(F)F.C([N+]1C=CN(C)C=1)CCC.[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].F[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=1[CH3:37]>CC#N>[C:18]([N:21]1[CH2:26][CH2:25][N:24]([C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=2[CH3:37])[CH2:23][CH2:22]1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 837951-AcetylpiperazineHCID 27341741-Butyl-3-methylimidazolium hexafluorophosphate

Product 1

HCID 53030571-Acetyl-4-(2-methyl-4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

1-Butyl-3-methylimidazolium hexafluorophosphate (1.75 g, 7.7 mmol) and acetyl piperazine (39.7 g, 309.4 mmol) was added to a stirred solution of 2-fluoro-5-nitrotoluene (12 g, 77.4 mmol) in MeCN (3 mL) and heated to 85° C. for 2 h. The reaction was cooled and concentrated in vacuo. Water (100 mL) was added to the resulting residue and the reaction extracted with EtOAc (3×100 mL). The solvent was dried (MgSO4), filtered, and concentrated in vacuo to yield the product as a yellow solid which was triturated with isohexane and dried in vacuo at 60° C.; 1H NMR δ 8.05 (2H, m), 7.14 (1H, d), 3.64-3.58 (4H, m), 3.05-2.94 (4H, m), 2.37 (3H, s), 2.37 (3H, s); MS m/e MH+ 264.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additionWater (100 mL) was added to the resulting residue
  4. extractionthe reaction extracted with EtOAc (3×100 mL)
  5. dry with materialThe solvent was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15ead006b72044e7ac3178e63cba7ace
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Linked notes

Loading…