Dicyclohexylcarbodiimide → 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

HRID 637682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637682
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:20]([OH:27])=[C:21]([CH2:23][C:24](O)=[O:25])[CH:22]=1>C(Cl)Cl>[Cl:16][C:17]1[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:20]2[O:27][C:24](=[O:25])[CH2:23][C:21]=2[CH:22]=1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 539130445-Chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid

Produkt 1

HCID 135769525-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 6.5 g (31.5 mmole) of dicyclohexyl carbodiimide in 40 ml of absolute methylene chloride is added at room temperature over a period of approximately 3 minutes to a solution of 8.1 g (30 mmole) of crude 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid in 50 ml of absolute methylene chloride. The reaction mixture is stirred for 30 minutes at room temperature. The precipitated dicyclohexylurea is filtered with suction and washed with methylene chloride. The filtrate is concentrated by evaporation in a vacuum rotary evaporator and the residue is chromatographed over silica gel using methylene chloride/hexane (1:1) as eluant. recrystallisation from hexane yields 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 129°-131°.

Aufarbeitung

  1. filtrationThe precipitated dicyclohexylurea is filtered with suction
  2. washwashed with methylene chloride
  3. concentrationThe filtrate is concentrated by evaporation in a vacuum rotary evaporator
  4. customthe residue is chromatographed over silica gel
  5. customrecrystallisation from hexane

Quellen und Nachweise

ORD-Eintrag
ord-1a867f40a79f4d23a8e7480012d19c6f
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04558043

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