3,5-Bis(trifluoromethyl)benzoyl chloride → HCID 53702005, compound

Participants

Reaction Conditions

Reaction Steps

2.49 g (9.0 mmol) of 3,5-bis-trifluoromethylbenzoyl chloride are added in the course of 1 hour at 0-5° C. to a stirred suspension of 2.50 g (9.0 mmol) of (2R*,4S*)-N-[2-(4-nitro-benzyl)-piperidin-4-yl]-acetamide in 20 ml of methylene chloride and 20 ml of a 10% aqueous sodium hydrogen carbonate solution. The mixture is then stirred for 1 hour at 25° C. The organic phase is dried over sodium sulfate, concentrated to dryness by evaporation and chromatographed on silica gel with methylene chloride/methanol. The title compound is obtained in the form of a yellowish resin. TLC: methylene chloride/methanol/conc. ammonia (90:9:0.5) Rf =0.45. 1H-NMR (200 MHz, D2O): rotameric mixture. δ 8.28-7.08 (m, 7H), 5.41 (br d, NH), 5.36-5.20 (m, 0.5H), 4.87-4.73 (m, 0.5H), 4.51-4.30 (m, 1H), 4.00-3.82 (m, 0.5H), 3.60-2.85 (m, 3.5H), 1.98 (s, 3H), 2.30-1.92 (m, 2H), 1.62-1.22 (m, 2H).

Provenance & Evidence