1-Benzyl-4-piperidone → HCID 178429194, Verbindung

Temperatur

110 °C

A mixture of 1-benzyl-4-piperidone (19.6 mL, 106 mmol), acetoacetamide (11.7 g, 116 mmol) in Eaton's reagent (40 mL) was allowed to stir at 110° C. After stirring for 18 h, the reaction mixture was cooled to rt, and then slowly poured into stirred aq NaHCO3 (150 g of NaHCO3 in 1000 mL of water. The mixture was diluted with DCM (1000 mL) and H2O (50 mL), and the two phases were separated. The products were extracted once with DCM (500 mL) from the aqueous layer. The combined organic layer was washed with brine (500 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The brown residue was triturated with acetone (200 mL). The precipitated solid was collected on a funnel, washed with acetone (100 mL), and dried under reduced pressure to give 6-benzyl-4-methyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-ol. 1H NMR (400 MHz, CDCl3) δ ppm 12.71 (br s, 1 H), 7.26-7.35 (m, 5 H), 6.22 (s, 1 H), 3.71 (s, 2 H), 3.34 (s, 2 H), 2.70-2.73 (m, 2 H), 2.77-2.79 (m, 2 H), 2.03 (s, 3 H); MS (ESI+) m/z 255.42 (M+H)+.

1. stirringAfter stirring for 18 h
2. temperaturethe reaction mixture was cooled to rt
3. additionslowly poured
4. customthe two phases were separated
5. extractionThe products were extracted once with DCM (500 mL) from the aqueous layer
6. washThe combined organic layer was washed with brine (500 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe brown residue was triturated with acetone (200 mL)
11. customThe precipitated solid was collected on a funnel
12. washwashed with acetone (100 mL)
13. customdried under reduced pressure

ORD-Eintrag

ord-7f8ebd9058c44e25a610796c4d0b6ad6

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846656B2