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Dicyclohexylcarbodiimide → 1-(3-pyridyl)-2-(N-(2-(3,4-dichlorophenyl)acetyl)-N-propylamino)ethanol

HRID 227282
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 227282
[CH:1]1(N=C=NC2CCCCC2)CCCC[CH2:2]1.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25]([OH:27])=O)[CH:20]=[CH:21][C:22]=1[Cl:23].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]([OH:38])[CH2:35][NH:36][CH3:37])[CH:29]=1>C(Cl)Cl>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]([OH:38])[CH2:35][N:36]([C:25](=[O:27])[CH2:24][C:19]2[CH:20]=[CH:21][C:22]([Cl:23])=[C:17]([Cl:16])[CH:18]=2)[CH2:37][CH2:1][CH3:2])[CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 798743,4-Dichlorophenylacetic acidHCID 224987342-(Methylamino)-1-(pyridin-3-yl)ethan-1-ol

Produkt 1

HCID 121638721-(3-pyridyl)-2-(N-(2-(3,4-dichlorophenyl)acetyl)-N-propylamino)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a flask containing 630 mg (3.1 mmol) of DCC (dicyclohexylcarbodiimide) was added 3 ml of methylene chloride and with stirring a solution of 625 mg (3.1 mmol) of 3,4-dichlorophenyl acetic acid in 5 ml of methylene chloride was added dropwise resulting in the formation of a precipitate. The reaction mixture was stirred for 5 minutes, and to it was added 550 mg (3.05 mmol) of 1-(3-pyridyl)-2-methylaminoethanol in 6 ml of methylene chloride, it was stirred further for 1 hour at 20° C. A precipitate formed was filtered off, and the resulting solution was evaporated. The evaporated filtrate was purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:CH3OH=10:0.5). This yields 0.56 g (50%) of 1-(3-pyridyl)-2-(N-(2-(3,4-dichlorophenyl)acetyl)-N-propylamino)ethanol in the form the oil (molecular weight: 367.278, gross formula: C18H20N2O2Cl2).

Aufarbeitung

  1. additionwas added dropwise
  2. customresulting in the formation of a precipitate
  3. stirringwas stirred further for 1 hour at 20° C
  4. customA precipitate formed
  5. filtrationwas filtered off
  6. customthe resulting solution was evaporated
  7. customThe evaporated filtrate was purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:CH3OH=10:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-3da898e69729456b8260a63820591ab2
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560474B2

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