Hydrochloric Acid → HCID 86603040, compound

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.

1. temperatureheated
2. temperatureto reflux over night
3. temperaturethe mixture was heated again
4. temperatureto reflux for 1.5 h
5. temperatureAfter cooling to rt
6. extractionthe mixture was extracted twice with EtOAc
7. washThe combined organic layers were washed with brine
8. dry with materialdried with magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customFinal purification (silica gel; DCM/methanol 95:5)

ORD record

ord-e277a5f52a3c4a4f81d0cd6d1f6decd7

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259183B2