Benzhydrylamine → 3-(Benzhydrylamino)-3-methylbutan-2-one

HRID 1437245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437245
Br[C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].[CH:8]([NH2:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO.C(N(CC)CC)C>[CH:8]([NH:21][C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 2

HCID 7036BenzhydrylamineHCID 3449113-Bromo-3-methyl-2-butanone

Produkt 1

HCID 103783013-(Benzhydrylamino)-3-methylbutan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To the above-obtained 3-bromo-3-methylbutan-2-one (5.88 g) in methanol (30 mL), benzhydrylamine (5.0 mL) and triethylamine (7.5 mL) were added. The resultant mixture was stirred at 70° C. for 24 hours, and then cooled in air. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and to the solid, diethyl ether was added, and then insoluble matter was removed by filtration. The mother liquid was brought to the dryness under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give 3-(benzhydrylamino)-3-methylbutan-2-one as an oily product (3.3 g, 34%).

Aufarbeitung

  1. temperaturecooled in air
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  4. dry with materialdried over magnesium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was evaporated under reduced pressure
  7. additionto the solid, diethyl ether was added
  8. custominsoluble matter was removed by filtration
  9. customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1ba1062def9a4ca19e6b16ec356f0ab2
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622471B2

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