[Mg].II.Br[CH2:5][CH2:6][CH2:7]C.[CH2:9]([N:16]1[CH2:21][CH2:20][C:19]([N:24]([CH3:26])[CH3:25])([C:22]#N)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH4+].[Cl-]>CCOCC.C1COCC1.CO.C(Cl)(Cl)Cl>[CH2:9]([N:16]1[CH2:17][CH2:18][C:19]([CH2:22][CH2:5][CH2:6][CH3:7])([N:24]([CH3:25])[CH3:26])[CH2:20][CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
To a mixture of 17.7 g (6 equiv.) of magnesium and 50 ml of dry ether there were added first a small amount of iodine and then, over a period of 1 hour, 100 g (6 equiv.) of bromobutane dissolved in 100 ml of dry ether. This reaction mixture was stirred for 1 hour at room temperature. The Grignard reagent prepared above was added over a period of 20 minutes to a solution of 30 g (1 equiv.) of 1-benzyl-4-(dimethylamino)piperidine-4-carbonitrile dissolved in 210 ml of dry THF, and the resulting reaction mixture was then stirred for 12 hours at room temperature. 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 filtered over Celite and extracted with ethyl acetate (3×200 ml), and the combined organic phases were dried over Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (aluminium oxide neutral; hexane). 18.2 g (53%) of product were obtained in the form of an oil.
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