Sodium Iodide → HCID 9801794, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-(2-chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole (0.28 g, 0.769 mmol) in dry DMF (6 mL) is added sodium iodide (0.09 g, 0.6 mmol), potassium carbonate (0.207 g, 1.5 mmol), and piperidine (0.13 g, 1.5 mmol). The mixture is heated at 70° C. for 6 h and then at room temperature for 18 h. The mixture is then partitioned between water and ether. The ether layer is washed three times with water (80 mL). The organic layer is dried over sodium sulfate and concentrated. Column chromatography (50 mL) silica gel using 1% methanol in CH2Cl2 as eluent gave 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl 2-(1-piperidinyl)ethyl ether (TLC: acetone/hexane, 20/80, Rf=0.42) which is converted to the methanesulfonate salt to give 0.134 g (34%) of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl 2-(1-piperidinyl)ethyl ether.

Provenance & Evidence