Cyanogen Chloride → 1-Cyano-4-hydroxy-2,2,6,6-tetramethyl piperidine

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Reaction Steps

62.8 g (0.4 mole) of 4-hydroxy-2,2,6,6-tetramethyl piperidine are dissolved in 250 ml of methylene chloride a solution of 16 g (0.4 mole) of sodium hydroxide in 250 ml of water is introduced and 20.5 ml of cyanogen chloride are added dropwise to the mixture at 0° to 5° C. The mixture is stirred until it reaches room temperature, after which the organic phase is separated off, dried with sodium sulphate, filtered and the methylene chloride distilled off, leaving 31 g (42.5% of the theoretical) of 1-cyano-4-hydroxy-2,2,6,6-tetramethyl piperidine. Bp 0.5 = 135° C; melting point 96°-98° C.

Provenance & Evidence