Sodium hydride → Tert-butyl 4-(2-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Participants

Reaction Steps

A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (9.298 g, 38.4 mmol) and 2-chlorophenylacetonitrile (5.0 g, 32.0 mmol) in a 4:1 mixture of THF/DMF (15 mL) was treated with NaH (2.82 g, 70.4 mmol) at 60 OC (7 d). The solvent was removed in vacuo, the residue dissolved in EtOAc (200 ml) and washed with saturated NaHCO3 (50 ml), H2O (2×50ml), and saturated aqueous NaCl (50 ml), dried Na2SO4) and concentrated in vacuo. Trituration of the residue with 100% MeOH afforded 4-(2-chlorophenyl)4-cyano-N-(1,1-dimethylethoxy) carbonyl piperidine as a white solid.

Provenance & Evidence