Reaktionsgleichung
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[N:10]1([C:16](=[O:19])[CH2:17][CH3:18])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C>[C:16]([N:10]1[CH2:15][CH2:14][N:13]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:12][CH2:11]1)(=[O:19])[CH2:17][CH3:18]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
To a high-pressure tube was added 6-bromopicolinaldehyde (1, 2.00 g, 10.7 mmol), 1-(piperazin-1-yl)propan-1-one (18, 3.82 g, 26.9 mmol), potassium carbonate (6.69 g, 48.4 mmol) and anhydrous DMF (12 mL). The tube was sealed and the reaction mixture was heated at 120° C. for 17 h. The reaction suspension was poured into water (100 mL) and the mixture was brought to pH 7 using 2 N aq. HCl (20 mL). The solution was extracted with CH2Cl2 (3×100 mL), washed with brine (300 mL), dried over Na2SO4, filtered and concentrated to a brown oil. The product was purified by silica gel chromatography eluting with 0-5% CH3OH in CH2Cl2 to afford the title compound (0.815 g, 31%) as an orange solid: 1H NMR (500 MHz, CDCl3) δ 9.89 (s, 1H), 7.68 (t, J=8.0 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 3.84-3.73 (m, 2H), 3.68-3.59 (m, 2H), 2.40 (q, J=7.5 Hz, 2H), 1.19 (t, J=7.5 Hz, 3H).
Aufarbeitung
- customThe tube was sealed
- extractionThe solution was extracted with CH2Cl2 (3×100 mL)
- washwashed with brine (300 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to a brown oil
- customThe product was purified by silica gel chromatography
- washeluting with 0-5% CH3OH in CH2Cl2
Quellen und Nachweise
- ORD-Eintrag
- ord-b6ecaa31adf24f61b19f43ae085f1262
- Quelldatensatz
- uspto-grants-2016_03
- Patentnummer
- US09278940B2
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