1-Phenyl-2-propen-1-one → 1,3-Dimethyl-3-(3-oxo-3-phenyl-propyl)-piperidin-4-one

Temperature

25 °C

To a stirred solution of 1,3-dimethyl-piperidin-4-one (0.1 g, 0.787 mmol) in mixture of 1,4 dioxane (2 mL) and water (0.1 mL) was added crushed KOH (44 mg, 0.787 mmol). The reaction mixture was stirred at 25° C. for 10 min. To this was added 1-phenylprop-2-en-1-one (103 mg, 0.787 mmol) dropwise. The reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water (10 mL) and EtOAc (20 mL), the organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by column chromatography on neutral alumina (eluted with EtOAc:Hexanes, 1:99) to afford 1,3-dimethyl-3-(3-oxo-3-phenyl-propyl)-piperidin-4-one as an oil (22 mg).

1. additionwas added
2. stirringThe reaction mixture was stirred at 25° C. for 2 h
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additionthe residue was diluted with water (10 mL) and EtOAc (20 mL)
5. customthe organic layer was separated
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe resulting crude product was purified by column chromatography on neutral alumina (eluted with EtOAc:Hexanes, 1:99)

ORD record

ord-0c551d20fef6440ca1f200327530665c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040519B2