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

HRID 538864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538864
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

Step-3: 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 it 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-029dc9d9b5fe42d0827ecb3f8f401052
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865752B2

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