1-Methyl-4-piperidone → HCID 89810863, compound

Temperature

-78 °C

5-Bromo-2-iodopyrimidine (2 g, 7.02 mmol) was dissolved in dry toluene (30 mL) and cooled to −78° C. under nitrogen. n-Butyllithium (2.5M solution in hexanes, 2.95 mL) was added dropwise, and the reaction mixture was stirred for 30 minutes before dropwise addition of 1-methylpiperidin-4-one (0.9 mL, 0.01 mol). The reaction mixture was stirred at −78° C. for 1 h. The reaction mixture was allowed to warm to room temperature, then diluted with 5% aqueous ammonium chloride solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (50 mL) and dried over magnesium sulphate, then the solvent removed under reduced pressure. The resulting crude material (1.55 g) was sonicated in ethyl acetate (10 mL) and DCM (1 mL), then heptane was added. The solid that formed was filtered to afford the title compound (580 mg, 29.4%) as a brown solid. LCMS Method F: MH+: m/z 272/274, RT 1.20 minutes.

1. temperatureto warm to room temperature
2. extractionextracted with ethyl acetate (3×50 mL)
3. washThe combined organic extracts were washed with brine (50 mL)
4. dry with materialdried over magnesium sulphate
5. customthe solvent removed under reduced pressure
6. customThe resulting crude material (1.55 g) was sonicated in ethyl acetate (10 mL)
7. additionDCM (1 mL), then heptane was added
8. customThe solid that formed
9. filtrationwas filtered

ORD record

ord-f83e72df333a40e7a14294b19305b3df

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2