Phenylacetonitrile → 1-Tert-butyl-4-phenylpiperidine-4-carbonitrile

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A solution of phenyl acetonitrile (1.0 g, 8.54 mmol) in DMSO (8 mL) was treated with sodium hydride (0.717 g, 29.88 mmol) portionwise. The resulting-suspension was stirred at 23° C. for 30 minutes. N,N-bis(2-chloroethyl)-2-methylpropan-2-amine (2.20 g, 9.39 mmol) was then slowly added over 5 minutes, then the suspension was heated at 65° C. overnight. The reaction was then diluted with 1N hydrochloric acid and washed with ethyl acetate (2×). The aqueous phase was basified with sat. aq. sodium carbonate and extracted with ethyl acetate (3×). The combined extracts were washed with water (5×), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil (1.40 g, 68%) which solidified on standing and was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 2.10-2.17 (3H, m), 2.31-2.37 (1H, m), 2.42 (3H, s), 2.47-2.57 (2H, m), 3.01 (2G, d, J=12.6 Hz), 7.45 (2H, dd, J=4.55 and 1.52 Hz), 8.68 (2H, dd, J=4.55 and 1.77 Hz).

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