Hydrochloric Acid → {[2-Chloro-4-fluoro-3-(trifluoromethyl)phenyl]methyl}amine hydrochloride

Temperature

60 °C

2-Chloro-4-fluoro-3-(trifluoromethyl)benzamide (0.490 g, 2.03 mmol) was treated with 1M borane in tetrahydrofuran (20.33 ml, 20.33 mmol) and stirred at 60° C. overnight. The mixture was then treated with 2N aqueous hydrogen chloride until gas evolution ceased and then stirred at 100° C. for 2 hrs. The mixture was reduced in vacuo and the residue was taken up in a minimum of water and washed with dichloromethane (30 ml). The pH of the aqueous layer was adjusted to pH11 by the addition of 2N aqueous sodium hydroxide solution and then extracted with dichloromethane (2×25 ml). The dichloromethane layers were separated using a hydrophobic frit, combined and evaporated in vacuo to leave a pale yellow oil. A 1M solution of hydrogen chloride in diethyl ether (3 ml, 3 mmol) was added and the resulting white solid was filtered off to give pure {[2-Chloro-4-fluoro-3-(trifluoromethyl)phenyl]methyl}amine hydrochloride (0.210 g) which was used without further purification.

1. stirringstirred at 100° C. for 2 hrs
2. washwashed with dichloromethane (30 ml)
3. additionThe pH of the aqueous layer was adjusted to pH11 by the addition of 2N aqueous sodium hydroxide solution
4. extractionextracted with dichloromethane (2×25 ml)
5. customThe dichloromethane layers were separated
6. customevaporated in vacuo
7. customto leave a pale yellow oil
8. filtrationthe resulting white solid was filtered off

ORD record

ord-c8a4ee171d6c411e8debc9a7d3a106f4

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718693B2