Sodium Iodide → 4-(1-Pyrrolidinylmethyl)-2-{4-[3-(1-pyrrolidinyl)propoxy]phenyl}-1,3-thiazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-thiazole ax72 (250 mg, 0.83 mmole, 1 eq) and pyrrolidine (0.3 ml, 3.6 mmol, 4.4 eq) is dissolved in acetonitrile (10 ml). Potassium carbonate (0.5 g, 3.6 mmole, 4.4 eq) and sodium iodide (25 mg, 0.17 mmole, 0.2 eq) are added. The solution is heated at 90° C. in a sealed tube for 48 h. After cooling, the solution is taken up in dichloromethane, washed with water and dried over magnesium sulfate. The crude material is purified by chromatography on silicagel (gradient: dichloromethane/methanol/ammonia 95:4.5:0.5 to 90:9:1) to provide 0.31 g of 4-(1-pyrrolidinylmethyl)-2-{4-[3-(1-pyrrolidinyl)propoxy]phenyl}-1,3-thiazole 73 as a brown oil.

Provenance & Evidence