Potassium Carbonate → HCID 20638934, Verbindung

HRID 565675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565675
CS(O[CH2:6][C@:7]1([CH3:19])[CH2:11][C:10]2[C:12]([CH3:18])=[CH:13][C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1)(=O)=O.[C:20]1([CH:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O>[CH3:19][C@@:7]1([CH2:6][N:31]2[CH2:32][CH2:33][CH:28]([NH:27][CH:26]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:29][CH2:30]2)[CH2:11][C:10]2[C:12]([CH3:18])=[CH:13][C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 13644890HCID 13644890, VerbindungHCID 86756224HCID 86756224, Verbindung

Produkt 1

HCID 20638934HCID 20638934, VerbindungAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
177 °C

Versuchsvorschrift

A suspension of (S)-(2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl methanesulfonate (0.34 g), N-(diphenylmethyl)-4-piperidinamine (0.73 g), and potassium carbonate (0.38 g) in N,N-dimethylacetamide (2 mL) was stirred under argon gas at 177° C. for 6 hours. This reaction mixture was diluted with water and extracted with diisopropyl ether. The organic layer was washed with water and extracted with 1N-hydrochloric acid. The aqueous layer was made basic with 2N-sodium hydroxide/water and extracted with diisopropyl ether. The extract was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to provide the title compound (0.49 g). Yield 79%.

Aufarbeitung

  1. extractionextracted with diisopropyl ether
  2. washThe organic layer was washed with water
  3. extractionextracted with 1N-hydrochloric acid
  4. extractionextracted with diisopropyl ether
  5. washThe extract was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Quellen und Nachweise

ORD-Eintrag
ord-99c95f5426d64c42a4fc1658333c567a
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172085B2

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