Triethylamine → HCID 66936517, compound

To a solution of (2R,5S)-2,5-dimethylpiperazine (commercially available) (3.495 g, 30 mmol) in dichloromethane (25 mL) at 0° C. was added triethylamine (3.76 mL, 27 mmol) followed by dropwise benzyl chloroformate (4.0 mL, 27 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The solvent was then evaporated to dryness. The residue was taken up in aqueous 1N HCl solution and washed with EtOAc. The organic layer was extracted with 1N HCl solution twice and the combined aqueous layers were basicified with 6N NaOH to ˜pH 11. The resulting basic aqueous solution was extracted with EtOAc three times. The combined organic layers were washed with brine, dried (MgSO4) and evaporated to yield phenylmethyl trans-2,5-dimethyl-1-piperazinecarboxylate (enantiomeric mixture) (1.35 g, 18%). LCMS: (M+H)+: 249.1.

1. customThe solvent was then evaporated to dryness
2. washwashed with EtOAc
3. extractionThe organic layer was extracted with 1N HCl solution twice
4. extractionThe resulting basic aqueous solution was extracted with EtOAc three times
5. washThe combined organic layers were washed with brine
6. dry with materialdried (MgSO4)
7. customevaporated

ORD record

ord-88d4c752330e47ada78dc6d1c54ffce0

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893056B2