1-(4-Pyridyl)piperazine → Ethyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

HRID 1290513

Reaktionsgleichung

Reaktionsgleichung von HRID 1290513
Br[CH2:2][C:3]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(#N)C>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:9][C:8]1[CH:16]=[CH:17][C:5]([C:3](=[O:4])[CH2:2][N:27]2[CH2:28][CH2:29][N:24]([C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH2:25][CH2:26]2)=[CH:6][CH:7]=1)[CH3:15]

Komponenten

4

Edukt 2

HCID 705171-(4-Pyridyl)piperazineHCID 18408936Ethyl 2-[4-(2-bromoacetyl)phenoxy]acetate

Produkt 1

HCID 18918266Ethyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 4-bromoacetylphenoxyacetate (6.0 g) was added to a stirred, cooled (4° C.) solution of 1-(4-pyridyl)piperazine (6.5 g) in acetonitrile (225 ml). Stirring was continued for 1 hour at 4° C., then overnight at ambient temperature when the precipitated solid was removed by filtration. The filtrate was evaporated in vacuo and the solid residue triturated with water, filtered, then washed with water and dried. Recrystallization from a small volume of ethanol gave the title compound, 1.71 g, as a cream coloured solid: m.p. 113°-114° C.; NMR (d6DMSO) δ8.15(2H,d), 7.98(2H,d), 7.02(2H,d), 6.80(2H,d), 4.89(2H,d), 4.17(2H,q), 3.84(2H,s), 3.32(4H,t), 2.62(4H,t) 1.22(3H,t); m/e 384 (M+H)+ ; calculated for C21H25N3O4 : C, 65.8; H, 6.6; N, 11.0. found: C, 65.5; H, 6.6; N, 10.8%.

Aufarbeitung

  1. customovernight at ambient temperature when the precipitated solid was removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe solid residue triturated with water
  4. filtrationfiltered
  5. washwashed with water
  6. customdried
  7. customRecrystallization from a small volume of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ca3c42b492ea439fa1bd5336aa38c091
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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