Cyclohexylamine → (S)-2-(4-(cyclohexylamino)phenyl)-4-((R)-1-phenylethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

To a suspension of (2S)-2-(4-bromophenyl)-4-((1R)-1-phenylethyl)morpholine (7.62 g, 22.0 mmol), palladium acetate (198 mg, 0.88 mmol), 2-(di-t-butylphosphino) biphenyl (525 mg, 1.76 mmol), and sodium tert-butoxide (2.96 g, 30.8 mmol) in toluene (40 ml) was added cyclohexylamine (3.78 ml, 33.0 mmol) at room temperature. After heating at 90° C. for 2.5 hours, the resulting suspension was passed through a Celite column. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography eluting 5-25% of ethyl acetate in hexane to afford (S)-2-(4-(cyclohexyl-amino)phenyl)-4-((R)-1-phenylethyl)morpholine (6.95 g, 87%) as white crystals.

Provenance & Evidence