Sodium hydride → tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

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Reaction Steps

A suspension of 4.4 g of sodium hydride at a concentration of 60% in oil in 300 ml of THF is admixed rapidly at AT with 7.51 g of 4-chlorophenylacetonitrile and then with 12 g of tert-butyl bis(2-chloroethyl)carbamate, heated at 40° C. for 28 hours and then left with stirring at AT overnight. Saturated ammonium chloride solution is added to the reaction mixture, which is then concentrated under vacuum to remove the THF, after which the aqueous phase which remains is extracted with ether, the organic phase is washed with a buffer solution pH=2 and with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated under vacuum. This gives 12 g of the expected product, which is used as it is.

Provenance & Evidence