Triethylamine → HCID 15751485, compound

HRID 1974623Notes

Reaction equation

HRID 1974623 reaction equation
Cl[C:2]1[C:3]([F:15])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[NH:7][CH:8]1[CH2:10][CH2:9]1.[C:16]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)(=[O:18])[CH3:17].C(N(CC)CC)C>O>[C:16]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:11]=[C:6]([NH:7][CH:8]3[CH2:10][CH2:9]3)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=2[F:15])[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 837951-AcetylpiperazineHCID 15751484HCID 15751484, compound

Product 1

HCID 15751485HCID 15751485, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Chloro-N-cyclopropyl-4-fluoro-2-nitroaniline (3.5 g, 15.2 mmol) is heated with N-acetylpiperazine (3.89 g, 30.4 mmol) and triethylamine (2.3 g 22.8 mmol) while stirring vigorously and held at 60° for 12 hours. The mass obtained is dissolved in water (200 ml) and extracted with ethyl acetate. The organic phase is washed with 10 percent sodium chloride solution and then dried over magnesium sulfate. After distillation of the solvent the residue is recrystallized from ethanol. There are obtained 4.57 g (93%) of 1-acetyl-4-[5-(cyclopropylamino)-2-fluoro-4-nitrophenyl]piperazine with a m.p. of 142°-143°.

Workup

  1. customThe mass obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with 10 percent sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationAfter distillation of the solvent the residue
  6. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-2c59982cdd3840c8ac6b6a8db5021e59
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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