Dimethylamine → N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide

HRID 1894748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894748
Br[CH:2]([CH2:15][CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)=[O:4].[CH3:17][NH:18][CH3:19].CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl.CO>[CH3:17][N:18]([CH3:19])[CH:2]([CH2:15][CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 63386157N-[4-(2-bromobutanoyl)phenyl]acetamide

Produkt 1

HCID 86681892N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of N-(4-(2-bromobutanoyl)phenyl)acetamide (4.80 g, 16.9 mmol) in 30 mL CHCl3 and 30 mL MeOH was treated with 16.9 mL dimethylamine in MeOH (2M, 33.8 mmol) and DIPEA (2.90 mL, 16.9 mmol). After stirring at rt for 48 hr, the mixture was concentrated in vacuo and the residue partitioned between DCM and saturated NaHCO3. The aqueous phase was extracted with DCM three times. The combined organic extracts were dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluting with 6% MeOH (2N NH3)/DCM to provide N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide as a light brown oil. MS ESI: m/z 249.19 [M+1+].

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM and saturated NaHCO3
  3. extractionThe aqueous phase was extracted with DCM three times
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 6% MeOH (2N NH3)/DCM

Quellen und Nachweise

ORD-Eintrag
ord-f32815d5d93445389764970dc56bc002
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513291B2

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