was added to the mixture and the organic layer was washed with 50 ml of saturated sodium chloride solution twice then the organic layer was dried on anhydrous sodium sulfate and evaporated to dryness the residue was purified by column chromatography silica gel petroleum ether ethyl acetate 150 1 to afford 10 8 g product as a white flocculent solid in 89 yield 1 h nmr 300 mhz cdcl 3 u03b4 11 37 s 1h 7 70 dd j 3 3 7 8 hz 1h 7 56 dd j 3 3 8 7 hz 1h 3 98 s 3h ms esi m h m z 297 0 55 100 ml of dimethylamine aqueous solution was added into a 250 ml round bottom flask 12 g 40 mmol of p iodobenzyl bromide compound 9 was added in three batches and stirred overnight at room temperature the reaction mixture was extracted using ethyl acetate for three times on the next day the organic layer was dried on anhydrous sodium sulfate and evaporated to dryness by rotary evaporator 8 4 g of yellow liquid was obtained by column chromatography silica gel petroleum ether ethyl acetate 5 to 1 in 80 yield 1 hnmr 300 mhz cdcl 3 u03b4 7 63 d j 8 1 hz 2h 7 05 d j 8 1 hz 2h 3 35 s 2h 2 22 s 6h ms esi m h m z 262 0 100 9 03 g 34 5 mmol of n n dimethyl 1 4 iodophenyl methylamine compound 10a.