Triethylamine → HCID 69119459, compound

Participants

Reaction Steps

To a stirred solution of (R)-[(2S,5R)-2-methyl-5-methyl-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (J. Med. Chem., 1999, 42, 2741-2746) (400 mg, 1.57 mmol) and triethylamine (0.4 ml, 2.84 mmol) in EtOAc (25 ml) was added a solution of 4-dimethylcarbamoylbenzoyl chloride (350 mg, 1.66 mmol) in EtOAc (25 ml). The resultant mixture was stirred at ambient temperature for 24 hours, washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was chromatographed on silica with EtOAc as eluent to give the title compound as a solid (120 mg, 0.28 mmol). NMR: 1.1-1.13 (m, 6H), 1.6 (s, 3H), 2.9 (s, 3H), 3.1 (s, 3H), 3.25 (m, 1H), 3.4 (m, 1H), 4.25 (s, 2H), 4.65 (s, 1H), 4.9 (s, 1H), 5.2 (s, 1H), 7.3-7.4 (dd, 4H); m/z 428.

Provenance & Evidence