Morpholine → HCID 59457474, compound

Participants

Reaction Steps

To a solution of 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid i106 (1.6 mmol, 1 eq, 0.5 g), triethylamine (3.2 mmol, 2 eq, 0.45 ml) in dichloromethane (20 ml) is added 1-hydroxybenzotriazole (0.32 mmol, 0.2 eq, 43 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (1.76 mmol, 1.1 eq, 0.33 g) and morpholine (1.92 mmol, 1.2 eq, 0.17 g). The mixture is stirred at room temperature overnight. The organic layer is washed with water and with a saturated aqueous solution of ammonium chloride, then dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure. The crude product is purified by flash chromatography over silicagel (eluent: dichloromethane/ethanol 99:1 to 95:5) to afford 380 mg of 4-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}carbonyl)morpholine i107.

Provenance & Evidence