1,2-Dichloroethane → 1-(2,4-Dimethoxyphenylacetyl)-4-(2-methylphenyl)piperazine

HRID 1292334

Reaktionsgleichung

Reaktionsgleichung von HRID 1292334
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][C:25](O)=[O:26].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][C:25]([N:11]1[CH2:12][CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:9][CH2:10]1)=[O:26]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 919652-MeppHCID 3505552-(2,4-Dimethoxyphenyl)acetic acid

Produkt 1

HCID 82970911-(2,4-Dimethoxyphenylacetyl)-4-(2-methylphenyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(2-methylphenyl)piperazine (.087 g, 0.41 mmol) and 2,4-dimethoxyphenylacetic acid (0.096 g, 0.49 mmol) were dissolved in 20 DMF (5 ml) and treated with EDC (0.091 g, 0.47 mmol) and HBT (0.071 g, 0.52 mmol). Triethylamine was added to the stirred mixture to bring the pH (moistened E. Merck colorpHast indicator) to ca. 9. The mixture was stirred at ambient temperature for 18 hours, then concentrated in vacuo. The residue was taken up in ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and the filtrate was concentrated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 1.5% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo to give the title compound.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. washthe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated to dryness in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 1.5% methanol in methylene chloride
  8. customThe combined product fractions were evaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6c0f53a3127d4a04baf5e948c80f9ef1
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756504

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