Morpholine → (4-Bromo-2-nitro-phenyl)-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-amine

Participants

Reaction Conditions

Reaction Steps

In a 250 mL flask, mix toluene-4-sulfonic acid 2-(4-bromo-2-nitro-phenylamino)-2-methyl-propyl ester (19.5 g, 44 mmol) and morpholine (50 mL). Heat at 100-110° C. for 2 days. Follow the progress of the reaction by HPLC. Cool the reaction and partition between water and EtOAc. Wash the organic layer with water (2×), dry (MgSO4) and concentrate to give 14 g dark oil. Recrystallize from heptane (400 mL) to give 11 g that is 80% pure by HPLC. Recrystallize a second time to give 6.6 g (42%) orange crystals; MS (es) 358, 360 (M+1), HPLC (ISO80-10M) t=3.17 (94%).

Provenance & Evidence