Triethylamine → 4-{[4-Methyl-2-(trifluoromethyl)phenyl]carbonyl}-2-piperazinone

2-piperazinone (0.400 g, 4 mmol, commercially available from e.g. Sigma-Aldrich) was dissolved in dichloromethane (DCM) (20 mL), and to this was added triethylamine (0.669 mL, 4.80 mmol). The solution was then cooled to 0° C. before 4-methyl-2-(trifluoromethyl)benzoyl chloride (I62) (0.979 g, 4.40 mmol) in dichloromethane (DCM) (5 mL) was added dropwise. The solution was stirred, under argon, for 30 minutes before the solvent was evaporated in vacuo. The remaining residue was then re-dissolved in DCM (40 mL) and washed with water (20 mL), a saturated solution of sodium bicarbonate (20 mL) and brine (20 mL), before being dried over anhydrous sodium sulphate. The sodium sulphate was then removed by filtration and the solvent was evaporated in vacuo. The remaining solid was then stirred in hexane (40 mL) at 55° C. for 30 minutes. The solid was then removed by filtration to yield the product in 1.110 g.

1. additionwas added dropwise
2. customwas evaporated in vacuo
3. dissolutionThe remaining residue was then re-dissolved in DCM (40 mL)
4. washwashed with water (20 mL)
5. dry with materiala saturated solution of sodium bicarbonate (20 mL) and brine (20 mL), before being dried over anhydrous sodium sulphate
6. customThe sodium sulphate was then removed by filtration
7. customthe solvent was evaporated in vacuo
8. stirringThe remaining solid was then stirred in hexane (40 mL) at 55° C. for 30 minutes
9. customThe solid was then removed by filtration
10. customto yield the product in 1.110 g

ORD record

ord-e4247b1912ab4cfd9df086607d116809

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2