Potassium Carbonate → Methyl 6-((2-ethylhexyl)(phenyl)amino)hexanoate

HRID 607493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 607493
[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O.CN(C)C=O>[CH2:26]([CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH3:27]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 868042-Ethylhexyl bromideHCID 20441676Methyl 6-(phenylamino)hexanoate

Produkt 1

HCID 57857730Methyl 6-((2-ethylhexyl)(phenyl)amino)hexanoateAusbeute 53.069,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a three-neck flask, methyl 6-(phenylamino)hexanoate (25.0 g, 0.113 mmol) and potassium carbonate (25.0 g, 0.169 mol) were added to dimethylformamide (100 ml) and stirred. The mixture was heated to 100° C., added with 3-(bromomethyl)heptane (26.2 g, 0.135 mol), and allowed to react with stirring for 12 hours. The reaction product was transferred into a separate funnel, and was then added with water and ethyl acetate, after which the organic layer was isolated therefrom, dehydrated using sodium sulfate, and then distilled under reduced pressure. Subsequently, the obtained material was separated through silica column chromatography, thus obtaining 20.0 g of a yellowish transparent liquid.

Aufarbeitung

  1. customto react
  2. stirringwith stirring for 12 hours
  3. customThe reaction product was transferred into a separate funnel
  4. customafter which the organic layer was isolated
  5. distillationdistilled under reduced pressure
  6. customSubsequently, the obtained material was separated through silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60022c30d19b4cdf9a31f0afe1b3f257
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915428B2

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