Triethylamine → HCID 66599167, compound

2-piperazinone (1 g, 9.99 mmol, commercially available from e.g. Sigma-Aldrich) was then dissolved in dichloromethane (DCM) (40 mL), and to this was added triethylamine (2.78 mL, 19.98 mmol). The solution was cooled to 0° C. before 2-chloro-4-fluoro-3-methylbenzoyl chloride, (2.072 g, 10.99 mmol), from Step 1, in DCM (10 mL) was added dropwise over 1 minute. The solution was then allowed to stir at room temperature for a further 30 minutes before the solvent was evaporated in vacuo. The remaining solid was then re-dissolved in DCM (80 mL) before being washed with water (30 mL), a saturated solution of sodium bicarbonate (30 mL), and brine (30 mL). The solution was then dried over anhydrous sodium sulphate, which was hen removed by filtration and the solvent was evaporated in vacuo. The remaining solid was then stirred in hexane at 55° C. for 30 minutes, before being filtered off to yield the product in 2.496 g.

1. additionwas added dropwise over 1 minute
2. customwas evaporated in vacuo
3. dissolutionThe remaining solid was then re-dissolved in DCM (80 mL)
4. washbefore being washed with water (30 mL)
5. dry with materialThe solution was then dried over anhydrous sodium sulphate, which
6. customremoved by filtration
7. customthe solvent was evaporated in vacuo
8. stirringThe remaining solid was then stirred in hexane at 55° C. for 30 minutes
9. filtrationbefore being filtered off
10. customto yield the product in 2.496 g

ORD record

ord-4e37aafcba6c466ab2420bb3c471f949

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2