Hydrochloric Acid → HCID 12988961, Verbindung

HRID 1070718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070718
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[CH:24]([O:26]CCCC)=[CH2:25].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C(Cl)Cl.CCN(CC)CC>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([C:24](=[O:26])[CH3:25])[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 812191,3-Bis(diphenylphosphino)propaneHCID 12988960HCID 12988960, Verbindung

Produkt 1

HCID 12988961HCID 12988961, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of trifluoro-methanesulfonic acid 3-(1-propyl-piperidin-4-yl)-phenyl ester (300 mg) in DMF (4 ml) under argon atm at r.t. was subsequently added NEt3 (356 μL), butyl vinyl ether (823 μL), 1,3-bis(diphenylphosphino)propane (50 mg), and Pd(OAc)2 (19 mg). The reaction mixture was then heated to 80° C. and after 2 h the reaction was stopped. 5% Hydrochloric acid solution (6 ml) was added and the combined mixture stirred for 45 min. Then CH2Cl2 was added and the phases were separated. The aqueous layer was then extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by flash chromatography (MeOH:CH2Cl2 (1:9 (v/v)). Collection of the fractions containing pure product and evaporation of the solvent afforded pure 1-[3-(1-Propyl-piperidin-4-yl)-phenyl]-ethanone (35 mg). MS m/z (rel. intensity, 70 eV) 245 (M+, 4), 216 (bp), 100 (19), 70 (36), 57 (13).

Aufarbeitung

  1. customat r.t.
  2. customthe phases were separated
  3. extractionThe aqueous layer was then extracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was purified by flash chromatography (MeOH:CH2Cl2 (1:9 (v/v))
  8. customCollection of the fractions
  9. additioncontaining pure
  10. customproduct and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-387439f4bee64df1966f38a110528ef3
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903120B2

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