N,N'-Dimethylethylenediamine → 4-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

Participants

Reaction Conditions

Reaction Steps

Intermediate 5 (1.075 g, 3.5 mmol), morpholin-3-one (389 mg, 3.85 mmol), CuI (67 mg, 0.35 mmol), N,N′-dimethylethylene diamine (75 μl, 0.7 mmol) and K2CO3 (1,064 g, 7.7 mmol) were suspended in toluene (30 ml) under argon and heated to 110° C. for 20 h. After cooling to RT the reaction mixture was quenched by addition of 100 ml sat. aq NH4Cl, 150 ml conc. NH3 in water and 100 ml water and extracted three times with ethyl acetate. The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with MgSO4, filtered and evaporated to dryness. The resulting oil crystallizes upon standing and was triturated with n-heptane-MTBE (19:1).

Provenance & Evidence