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

HRID 32646

Reaktionsgleichung

Reaktionsgleichung von HRID 32646
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

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 silicagel (eluent: heptane/ethylacetate 0%-20% (10 minutes) to provide the title compound (69 mg, 68%) as a light yellow solid, MS (m/e): 390.2 (MH+, 100%)

Aufarbeitung

  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 silicagel (eluent

Quellen und Nachweise

ORD-Eintrag
ord-1895dfa81431463490583c1a94a66577
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427612B2

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