1-Methylpiperazine → N-ethyl-4'-fluoro-5'-(4-methyl-1-piperazinyl)-2'-nitroacetanilide

HRID 1974619Notes

Reaction equation

HRID 1974619 reaction equation
Cl[C:2]1[C:3]([F:17])=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([CH:13]=1)[N:7]([CH2:11][CH3:12])[C:8](=[O:10])[CH3:9].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[CH2:11]([N:7]([C:8](=[O:10])[CH3:9])[C:6]1[CH:13]=[C:2]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[C:3]([F:17])=[CH:4][C:5]=1[N+:14]([O-:16])=[O:15])[CH3:12]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 157514805'-chloro-N-ethyl-4'-fluoro-2'-nitroacetanilide

Product 1

HCID 15751481N-ethyl-4'-fluoro-5'-(4-methyl-1-piperazinyl)-2'-nitroacetanilideYield 78,488.297%

Procedure

5'-Chloro-N-ethyl-4'-fluoro-2'-nitroacetanilide (74 g, 0.284 mmol) is treated with N-methylpiperazine (126 ml, 1.13 mol) and the solution obtained is stirred at 60° for 2 hours. The reaction mixture is evaporated, the residue is dissolved in ethyl acetate (250 ml) and washed in succession with water (3×100 ml) and 10 percent sodium chloride solution (100 ml). The organic solution is dried over magnesium sulfate and evaporated. The residue is recrystallized from ethyl acetate/n-hexane. There are obtained 72.3 g (78.5%) of N-ethyl-4'-fluoro-5'-(4-methyl-1-piperazinyl)-2'-nitroacetanilide with a m.p. of 117°-119°.

Workup

  1. customthe solution obtained
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in ethyl acetate (250 ml)
  4. washwashed in succession with water (3×100 ml) and 10 percent sodium chloride solution (100 ml)
  5. dry with materialThe organic solution is dried over magnesium sulfate
  6. customevaporated
  7. customThe residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-6f6b7726b1a8462fa57109b1885d6e30
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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