Hydrochloric Acid → 3-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-one

HRID 132220

Reaktionsgleichung

Reaktionsgleichung von HRID 132220
Cl.O[CH:3]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[NH:28][C:29](=[O:34])C(C)(C)C)[CH:4]([CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)C(OC)=O>O>[NH:12]1[CH2:11][CH2:10][CH:9]([C:4]2[C:29](=[O:34])[NH:28][C:27]3[C:22]([CH:3]=2)=[CH:23][N:24]=[CH:25][CH:26]=3)[CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59732007tert-Butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(4-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 597319443-(piperidin-4-yl)-1,6-naphthyridin-2(1H)-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Concentrated hydrochloric acid (8.0 mL, 97 mmol) was added with stirring to a mixture of tert-butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(4-pivalamidopyridin-3-yl)propan-2-yl)piperidine-1-carboxylate (1.2 g, 2.6 mmol) and water (24 mL). Reaction was heated to reflux and held for 14 hours. Mixture was concentrated in vacuo. Residue was treated with acetonitrile (70 mL) and then concentrated in vacuo. Residue was crystallized from ethanol. Title compound was obtained as white solid in 77% yield. (M+H)+=230.1.

Aufarbeitung

  1. customReaction
  2. temperaturewas heated
  3. temperatureto reflux
  4. concentrationMixture was concentrated in vacuo
  5. additionResidue was treated with acetonitrile (70 mL)
  6. concentrationconcentrated in vacuo
  7. customResidue was crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-948e54cfa62a4ae8bf8c4150001aeecf
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384930B2

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