Diethyl Ether → 7-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one

HRID 501988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501988
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:23][C:22]3[C:17](=[CH:18][C:19]([F:24])=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:25])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(OCC)C>C(O)C.[Pd]>[F:24][C:19]1[CH:18]=[C:17]2[C:22]([CH2:23][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15](=[O:25])[NH:16]2)=[CH:21][CH:20]=1

Komponenten

5

Edukt 2

HCID 3283Diethyl EtherHCID 594243183-(1-Benzylpiperidin-4-yl)-7-fluoro-3,4-dihydroquinazolin-2(1H)-one

Produkt 1

HCID 594242967-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

3-(1-Benzylpiperidin-4-yl)-7-fluoro-3,4-dihydroquinazolin-2(1H)-one (1.32 g, 3.89 mmol) was dissolved in ethanol (100 mL) at room temperature. To this was added palladium (10% on charcoal, 130 mg). The resulting mixture was stirred under a hydrogen balloon for 4 d. The reaction was filtered through a pad of celite, eluting with ethanol (50 mL), and concentrated in vacuo to afford a yellow residue. Upon addition of diethyl ether (20 mL), a solid precipitated from solution. Trituration and filtration with diethyl ether (2×5 mL) gave the title compound as a yellow solid (0.842 g, 87% yield). 1H-NMR (CD3OD, 400 MHz) δ 6.94-6.88 (m, 2H), 6.78 (dd, J=6.2, 4.0, 1H), 4.42 (s, 2H), 4.41-4.35 (m, 1H), 3.53-3.47 (m, 2H), 3.21-3.13 (m, 2H), 2.25-2.14 (m, 2H), 1.98-1.92 (m, 2H). Mass spec.: 250.10 (MH+).

Aufarbeitung

  1. filtrationThe reaction was filtered through a pad of celite
  2. washeluting with ethanol (50 mL)
  3. concentrationconcentrated in vacuo
  4. customto afford a yellow residue
  5. customa solid precipitated from solution
  6. filtrationTrituration and filtration with diethyl ether (2×5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5619d445af7b4e4da7b2149af04dc27e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772244B2

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