3-Bromoanisole → 1-(3-Methoxyphenyl)piperidine-4-carbonitrile

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Reaction carried out by , work up and purification on this page. piperidine-4-carbonitrile (7.07 g, 64.16 mmol); 1-bromo-3-methoxybenzene (6.77 mL, 53.47 mmol) and diacetoxypalladium (2.401 g, 10.69 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.732 g, 2.14 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (123 mL, 122.97 mmol) and toluene (20 mL). The resultant mixture was stirred overnight at 100 °C (suspect that it did not need overnight. The reaction mixture was poured onto DCM (200 mL), the mixture was filtered through celite and evaporated to afford a black residue. This was suspended in EtOAc (200 mL) and water (20 mL) and filtered through a pad of silica, washing through with EtOAc (300 mL) and water (20 mL). The filtrate was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 1-(3-methoxyphenyl)piperidine-4-carbonitrile (3.29 g, 28.5 %) as a yellow oil which solidified on standing.

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