Hydrochloric Acid → HCID 86603040, compound

Participants

Reaction Steps

A solution of 680 mg N-[2-(3,4-dichloro-phenyl)-ethyl]-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-benzamide (1.48 mmol) in 10 ml of THF was added dropwise to 5.9 ml of a 1 molar solution of BH3-THF complex in THF at 0° C. The reaction mixture was stirred for 1 h at rt and then heated to reflux over night. Then 2 ml of 6 N HCl solution were added very carefully at ambient temperature and the mixture was heated again to reflux for 1.5 h. After cooling to rt, the pH was adjusted to 8-9 by addition of 1 N sodium hydroxide solution and the mixture was extracted twice with EtOAc. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. Final purification (silica gel; DCM/methanol 95:5) yielded 647 mg (98%) of [2-(3,4-dichloro-phenyl)-ethyl]-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-benzyl]-amine as a white solid.

Provenance & Evidence