Morpholine → 3-Chloro-5-morpholinoaniline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-bromo-5-chloroaniline (1.00 g, 4.84 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.19 g, 0.39 mmol), Pd2dba3 (0.177 g, 0.19 mmol) and morpholine (0.464 g, 5.33 mmol) in THF (9.70 mL). To this mixture was added LHMDS in THF (19.37 mL, 19.37 mmol) and the resulting reaction was heated to 65° C. Stirring continued for 2.5 h. After which the reaction was cooled to rt and then poured into water (100 mL) and extracted with EtOAc (2×150 mL) and DCM (2×150 mL). The combined organic layers were dried over magnesium sulfate and the crude product was purified on silica gel (0 to 100% DCM in EtOAc) to give 3-chloro-5-morpholinoaniline. Mass Spectrum (ESI) m/e=213.1 (M+1).

Provenance & Evidence