Dimethylformamide → HCID 18963350, compound

Temperature

0 °C

3-acetyl-1,4,5,6-tetrahydropyridine (20.0 g, 0.16 mole) was added under nitrogen to a mixture of sodium hydride (5.76 g, 0.24 mole) and dry dimethylformamide (50 ml) stirring at 0°C. and stirring was continued for 15 minutes 2-Bromopropane (21.5 g, 0.175 mole) was then added dropwise over 15 min, stirring continued for a further hour at 0°C. then overnight at room temperature. The reaction mixture was cautiously added to iced water (100 g) under nitrogen and extracted with diethyl ether (3×100 ml). The combined organic phase was extracted with water (150 ml), dried over magnesium sulphate, concentrated under reduced pressure to give methyl 1-(1-methylethyl)- 1,4,5,6-tetrahydro-3-pyridyl ketone (1). The product was distilled as a pale yellow oil (b.pt 97-98°C./0.5 mm Hg)

1. stirringstirring
2. stirringstirring
3. waitcontinued for a further hour at 0°C.
4. customovernight
5. customat room temperature
6. extractionextracted with diethyl ether (3×100 ml)
7. extractionThe combined organic phase was extracted with water (150 ml)
8. dry with materialdried over magnesium sulphate
9. concentrationconcentrated under reduced pressure

ORD record

ord-f043729637524e71a5e2f623fa53d760

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05000946