Aniline → N-phenylmorpholine-2-carboxamide

Participants

Reaction Steps

To a stirred solution of 4-{[(1,1-dimethylethyl)oxy]carbonyl}-2-morpholinecarboxylic acid (500 mg, 2.16 mmol) in dry DMF (2 mL) at 0° C. were added EDCI (456 mg, 2.38 mmol), HOBT (331 mg, 2.16 mmol) and aniline (0.22 mL, 2.38 mmol). The solution was stirred at room temperature overnight. The solvent was evaporated and the resulting residue was poured onto water and extracted with EtOAc (2×) and CH2Cl2 (2×). The combined organics were washed with brine and dried (MgSO4), filtered and evaporated. To this crude material dissolved in CH2Cl2/CH3OH (3 mL/0.3 mL) was added TFA (1.5 mL), and the reaction mixture was stirred at room temperature for 3 hours. The mixture was concentrated and dried in vacuo to afford a light brown oil. Et2O and hexanes were added and a precipitate crashed out. The mixture was sonicated and filtered to afford the title compound (604 mg). LC-MS (ES) m/z=207 [M+H]+.

Provenance & Evidence