Iodine → HCID 68409296, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 34.5 g (3.5 equiv.) of magnesium and 100 ml of dry diethyl ether there were added first a small amount of iodine and then, over a period of 10 minutes, 10 g (0.15 equiv.) of bromobenzene, and stirring was carried out for a further 10 minutes. When the reaction had started, 183 g (2.85 equiv.) of bromobenzene dissolved in 500 ml of diethyl ether were added dropwise over a period of 2 hours, and stirring was continued for 15 minutes. 100 g (1 equiv.) of 1-benzyl-4-(dimethylamino)piperidine-4-carbonitrile dissolved in 900 ml of diethyl ether were added over a period of 2 hours to the Grignard reagent prepared above, and finally the mixture was heated for 12 hours at 80° C. The progress of the reaction was monitored by thin-layer chromatography (10% MeOH/CHCl3). When the reaction was complete, the reaction solution was cooled to 0° C.; saturated NH4Cl solution was added, the mixture was extracted with ethyl acetate (3×300 ml) and the combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel; 1% MeOH/CHCl3). 30 g (35%) of product were obtained in the form of a yellow solid.

Provenance & Evidence