4-Methylmorpholine → 2-(3,4-Dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-(3-piperidin-1-yl-propyl)-propionamide

Participants

Reaction Steps

To a solution of (2,2-dimethoxy-ethyl)-(3-piperidin-1-yl-propyl)-amine (400 mg, 1.74 mmol) in N,N-dimethylformamide (4 mL) were added 2-(3,4-dichloro-phenylamino)-propionic acid (intermediate 11; 337 mg, 1.91 mmol), 4-methylmorpholine (527 mg, 5.21 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (990 mg, 2.61 mmol) at RT, then after 2 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH/25% aq. ammonia solution 90:10:0.25) afforded the title compound (545 mg, 70%). Yellow viscous oil, MS: 446.2 (M+H)+.

Provenance & Evidence