Iodine → HCID 67367347, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 31.2 g (5 equiv.) of magnesium and 100 ml of dry THF there were added first a small amount of iodine and then, over a period of 10 minutes, 10 g (0.25 equiv.) of bromobenzene, and stirring was carried out for a further 10 minutes. When the reaction had started, 194.2 g (4.75 equiv.) of bromobenzene dissolved in 500 ml of THF were added dropwise over a period of 2 hours, and stirring was then carried out for 15 minutes. 70 g (1 equiv.) of 1-benzyl-4-(pyrrolidin-1-yl)piperidine-4-carbonitrile dissolved in 450 ml of THF 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, extraction with ethyl acetate (3×200 ml) was carried out, and the combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, 33 g (40%) of crude product were obtained in the form of an oil.

Provenance & Evidence