Hydrochloric Acid → 4-(4-Oxopiperidin-1-yl)benzonitrile

HRID 842785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842785
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]C1C.Cl>CCOCC>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)#[N:18]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 57228643N-(4-Cyanophenyl)-4-piperidone propylene ketal

Produkt 1

HCID 110198874-(4-Oxopiperidin-1-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 34 (915 mg, 3.54 mmol) in ether (6 mL) was treated with 6N aqueous HCl (25 mL). The mixture was stirred at room temperature (2 d). The solvent was removed in vacuo and the residue dissolved in 3N HCl (25 mL) and acetic acid (20 mL). The mixture was stirred at room temperature (2 h). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium carbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (35).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in 3N HCl (25 mL)
  3. stirringThe mixture was stirred at room temperature (2 h)
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in dichloromethane
  6. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d791415aa9c44db9b016848b5efd37ae
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376503B1

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