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

HRID 864825

Reaktionsgleichung

Reaktionsgleichung von HRID 864825
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>[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][N:27]([CH2:2][C:3]([C:5]3[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:28][CH2:29]2)=[CH:20][CH:19]=1

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. Recrystallisation 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. customRecrystallisation from a small volume of ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3487e30caa4241b7a9d44c16a7af5429
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563141

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