4-(2,6-Difluoro-4-nitrophenyl)thiomorpholine → 3,5-Difluoro-4-(4-thiomorpholinyl)aniline

Participants

Reaction Steps

A solution of 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine (3.00 g, 11.5 mmol) in tetrahydrofuran (60 mL) is added to a Parr bottle containing a mixture of Raney nickel (1 g) in water (15 mL) under N2, and the reaction mixture is shaken on a Parr apparatus under a hydrogen atmosphere at 40 psi for 24 hrs. The catalyst is removed by filtration through Celite, rinsing with tetrahydrofuran and water, the filtrate is diluted with water (50 mL) and EtOAc (50 mL), and the layers are separated. The organic phase is washed with saline (25 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting oil is chromatographed on a Flash 40M 90 g silica gel cartridge eluting with EtOAc/heptane (15/85). Pooling and concentration of those fractions with an Rf=0.19 by TLC (EtOAc/hexanes, 25/75) gives the title compound, mp 85–86° C.; MS (ESI+) for C10H12N2F2S m/z 231 (M+H)+.

Provenance & Evidence