Tetrahydrofuran → HCID 68733876, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(phenylamino)piperidine-1-carboxylate (2.30 g, 8 mmol), 1-iodo-3-(trifluoromethyl)benzene (1 ml, 8 mmol), palladium(ii) acetate (0.07 g, 0.3 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.2 g, 0.3 mmol), and potassium tert-butoxide, 1.0M solution in tetrahydrofuran (1 ml, 10 mmol) in toluene (20 mL) was heated at 110° C. for 18 h. The reaction mixture was diluted with EtOAc, filtered, washed with 1N NaOH and brine, and the organic layer was concentrated under vacuum. Conc HCl (20 mL) was added to the residue and the solution was concentrated under vacuum. Conc HCl (20 mL) was added to the residue and the solution was stirred at RT for 8 h and concentrated. The pH was adjusted to 11 with the addition of 1N NaOH solution and the product was extracted with DCM. The DCM layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified with ISCO using 0-15% MeOH in DCM to give product N-phenyl-N-(3-(trifluoromethyl)phenyl)piperidin-4-amine (1.5 g, 56% yield).

Provenance & Evidence