Triethylamine → 1-{3-Fluoro-4-[4-(2-fluoro-5-nitrobenzoyl)piperazino]phenyl}-1-ethanone

HRID 2374249Notes

Reaction equation

HRID 2374249 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[F:21][C:22]1[CH:23]=[C:24]([C:34](=[O:36])[CH3:35])[CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>O1CCOCC1>[F:21][C:22]1[CH:23]=[C:24]([C:34](=[O:36])[CH3:35])[CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][N:31]([C:4](=[O:5])[C:3]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=2[F:1])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6856101-(3-Fluoro-4-piperazin-1-ylphenyl)ethanoneHCID 109765702-Fluoro-5-nitrobenzoyl chloride

Product 1

HCID 13622671-{3-Fluoro-4-[4-(2-fluoro-5-nitrobenzoyl)piperazino]phenyl}-1-ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-Fluoro-5-nitro-benzoyl chloride (CAS: 7304-32-7; Feng, Y.; Burgess, K.; Chem.Europ.J.; EN; 5; 11; 1999; 3261-3272) (0.054 g, 0.261 mmol) in dioxane (1 ml) was treated with triethylamine (0.073 ml, 0.522 mmol) and then with a solution of 1-(3-Fluoro-4-piperazin-1-yl-phenyl)-ethanone (CAS: 189763-57-3; WO9714690) (58 mg, 0.261 mmol) in dioxane (1 ml). The mixture was stirred at room temperature for 30 minutes. The solvent was removed in vacuo. The crude oil was taken in water. The aqueous layer was extracted 3 times with CH2Cl2. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude gum was purified on a SiO2 (Heptane/AcOEt 0%-20% (10 minutes, then 20% (5 minutes) to provide 1-{3-Fluoro-4-[4-(2-fluoro-5-nitro-benzoyl)-piperazin-1-yl]-phenyl}-ethanone (69 mg, 68%) as a light yellow solid (M+H+: 390.2).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe aqueous layer was extracted 3 times with CH2Cl2
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude gum was purified on a SiO2 (Heptane/AcOEt 0%-20% (10 minutes

Sources & evidence

ORD record
ord-65036bf60c5b4ca8b8e253634c072d25
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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