Potassium Carbonate → 3-(R)-(1-cyano-1,1-diphenylmethyl)-1-[2-(indan-5-yl)ethyl]piperidine

HRID 1584165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584165
[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].Br[CH2:23][CH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH2:30][CH2:29][CH2:28]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:23][CH2:24][C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[CH2:30][CH2:29][CH2:28]3)[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 212240805-(2-bromoethyl)-2,3-dihydro-1H-indeneHCID 228537583-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine

Produkt 1

HCID 228537513-(R)-(1-cyano-1,1-diphenylmethyl)-1-[2-(indan-5-yl)ethyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture containing 3-(R)-(+)-(1-cyano-1,1,-diphenylmethyl)-piperidine (0.28 g), 5-(2-bromoethyl)indane (0.23 g--see Preparation 4), anhydrous potassium carbonate (0.3 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (20 ml), the layers separated, and the aqueous layer extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with hexane containing dichloromethane (30% up to 70%) then dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from acetonitrile to give the title compound as colorless rhombs, yield 0.13 g, m.p. 88-91° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (20 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (3×20 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a gum which
  9. customwas purified by column chromatography on silica eluting with hexane
  10. additioncontaining dichloromethane (30% up to 70%)
  11. additiondichloromethane containing methanol (0% up to 5%)
  12. concentrationconcentrated in vacuo
  13. customto give an oil which
  14. customwas crystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a344f509afcc4e73aee56e91e4dc4112
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932594

Notizen zur Reaktion

Wird geladen…