Trifluoroacetic acid → HCID 59452651, compound

Participants

Reaction Conditions

Reaction Steps

1,1-Dimethylethyl 4-(1-{4-nitro-3-[(2,2,2-trifluoroethyl)oxy]phenyl}-4-piperidinyl)-1-piperazinecarboxylate (1.35 g, 2.76 mmol) was dissolved in 40 mL of DCM with stirring. TFA (10.0 mL, 130 mmol) was added via syringe, and the reaction was stirred for 3 h and cooled to 0° C. The reaction was quenched with 20 mL of 6N NaOH (aqueous). Saturated NaHCO3 (aqueous) was added until the pH was approximately 9. The mixture was poured into H2O and DCM. The layers were separated, and the aqueous layer was washed with 4:1 DCM/iPrOH (2×) and 4:1 EtOAc/iPrOH. The combined organic layers was dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash chromatography afforded 0.879 g (82%) of the title compound of step E. 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=9.5 Hz, 1H), 6.63 (dd, J=9.5, 2.4 Hz, 1H), 6.55 (d, J=2.4 Hz, 1H), 4.88 (q, J=8.7 Hz, 2H), 4.02 (d, J=13.6 Hz, 2H), 2.84-2.98 (m, 2H), 2.56-2.67 (m, 4H), 2.26-2.49 (m, 5H), 1.96 (br. s., 1H), 1.70-1.84 (m, 2H), 1.38 (d, J=8.2 Hz, 2H).

Provenance & Evidence