1,1'-Carbonyldiimidazole → HCID 15645953, Verbindung

HRID 1196875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196875
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([OH:24])=O)[CH:17]=[CH:18][C:19]=1[Cl:20].[C:25]1([CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH:34]([CH2:38][OH:39])[CH2:33]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([N:35]2[CH2:36][CH2:37][N:32]([CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:33][CH:34]2[CH2:38][OH:39])=[O:24])[CH:17]=[CH:18][C:19]=1[Cl:20]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 2756656(4-benzylpiperazin-2-yl)methanol

Produkt 1

HCID 15645953HCID 15645953, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

1,1'-Carbonyldiimidazole (236 mg) was added to a stirred solution of 3,4-dichlorophenylacetic acid (314 mg) in dry dichloromethane (6 ml) at room temperature under nitrogen. The resulting solution was stirred at room temperature for 1 h and added dropwise to a cooled solution of 4-(phenylmethyl)-2-piperazinemethanol (300 mg) in dry dichloromethane (3 ml) and stirred at room temperature for 19 h. The reaction mixture was diluted with dichloromethane (5 ml) and washed with 2N sodium carbonate solution (3×10 ml). The organic layer was dried and evaporated to give an oil which was purified by flash column chromatography using gradient elution from dichloromethane:ethyl acetate (2:1) to dichloromethane:ethyl acetate (1:1) to dichloromethane:methanol (9:1) to give the title compound as a solid (200 mg). m.p. 148°-150°.

Aufarbeitung

  1. stirringstirred at room temperature for 19 h
  2. washwashed with 2N sodium carbonate solution (3×10 ml)
  3. customThe organic layer was dried
  4. customevaporated
  5. customto give an oil which
  6. customwas purified by flash column chromatography
  7. washelution from dichloromethane:ethyl acetate (2:1) to dichloromethane:ethyl acetate (1:1) to dichloromethane:methanol (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-552eb85d65d44a6e9c0af3043c8eb57e
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116842

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