Potassium Cyanide → tert-butyl 4-[4-[(Z)-C-cyano-N-hydroxycarbonimidoyl]phenyl]piperazine-1-carboxylate

Participants

Reaction Steps

To tert-butyl 4-{4-[(E)-(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate (1.593 g, 5.22 mmol) in CH2Cl2 (25 mL) was gradually added Javex (approx. 10% NaOCl, 19.5 mL,.26.1 mmol) and the reaction mixture stirred for 1 hour. Potassium cyanide (3.4 g, 52.2 mmol) was added and the reaction stirred for 1 hour. The reaction was poured into brine and the product extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo with silica gel (to pre-adsorb product on silica gel) and purified by flash chromatography over silica gel (EtOAc/Hex, 1/1) to afford tert-butyl 4-(4-[(Z)-cyano(hydroxyimino)methyl]phenyl}piperazine-1-carboxylate.

Provenance & Evidence