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Potassium Carbonate → 2,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide

HRID 1587852
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1587852
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][NH:14][CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1)#[N:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH2:29][CH2:28][C:27]2[CH:31]=[CH:32][C:24]([C:22]#[N:23])=[CH:25][CH:26]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 128865484-(2-Bromoethyl)benzonitrileHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Produkt 1

HCID 190884772,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (1.0 g-see Preparation 3), 4-cyanophenethyl bromide (0.82 g), anhydrous potassium carbonate (2.0 g) and acetonitrile (30 ml) was heated under reflux for 10 hours. The mixture was partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×30 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was further purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 4%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.22 g.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. customThe mixture was partitioned between dichloromethane (50 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×30 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 6%)
  11. concentrationconcentrated in vacuo
  12. customto give an oil which
  13. customwas further purified by column chromatography on silica eluting with dichloromethane
  14. additioncontaining methanol (0% up to 4%)
  15. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-69906e987c394f07b3785cd0a3976b06
Quelldatensatz
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05219871

Notizen zur Reaktion

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