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Dimethylamine → 1-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester

HRID 448765
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 448765
[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[CH:16][CH:15]=2)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:22][NH:23][CH3:24]>>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:23]([CH3:24])[CH3:22])=[CH:16][CH:15]=2)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 2

HCID 674DimethylamineHCID 576728591-[[[4-(Chloromethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester

Produkt 1

HCID 576728621-[[[4-[(Dimethylamino)methyl]phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl esterAusbeute 50 %

Versuchsvorschrift

30 ml of 40% aqueous dimethylamine solution was added to 4.5 g (14.5 mmol) of 1-[[[4-(chloromethyl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid methyl ester, and the mixture was heated under reflux for 3 hours. The reaction solution was distilled off under reduced pressure, a saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, diisopropyl ether was added to the residue, and the mixture was stirred overnight. The precipitated solid was collected by filtration to obtain 2.3 g (50%) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe reaction solution was distilled off under reduced pressure
  4. additiona saturated aqueous sodium bicarbonate solution was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine, and it
  7. dry with materialwas dried with anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure, diisopropyl ether
  9. additionwas added to the residue
  10. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ecc1e472f8eb4aaf80f084e9bc14c61d
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481725B2

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