2-(Diisopropylamino)ethyl chloride → 4-Diisopropylamino-2-phenyl-butyronitrile

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Reaction Steps

Sodium hydride, 80% in mineral oil (2.82 g, 94 mmol), was washed with petroleum ether and dried under a N2-stream. Dry DMF (100 mL) was added. Benzyl cyanide (12.1 g, 103 mmol) was added to the stirred suspension over a period of 20 min. The temperature rose to approx. 45° C. The mixture was stirred for another 15 min. 2-Chloroethyl-diisopropylamine (15.4 g, 94 mmol) was added. All the amine was consumed within 30 min. Most of the DMF was evaporated under reduced pressure and the residue was dissolved in water/diethyl ether. The aqueous phase was extracted once with diethyl ether and the combined organic phases were extracted twice with 2 M HCl. The combined aqueous phases were made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were then dried (Na2SO4) and the solvent was evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine, 40:1), affording the title compound, 16.8 g (67%), as a colourless liquid. 1H NMR (CDCl3) δ1.01 (m, 12H), 1.97 (m, 2H), 2.62 (m, 2H), 3.00 (m, 2H), 4.02 (dd, 1H), 7.17-7.40 (m, 5H).

Provenance & Evidence