Sodium Hydroxide → 2-(4-n-Butylamino-2,2,6,6-tetramethylpiperidin-1-yl) ethanol

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Reaction Steps

A solution of 12.6 g (42.2 mmol) of N-n-butyl-N-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-yl]acetamide [Example 1bη2] in 180 ml of 2N hydrochloric acid is refluxed for 48 hours. The reaction mixture is then cooled 0°-5° C. and, after addition of 40 ml of 30% sodium hydroxide solution, extracted twice with toluene. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue over silica gel with the solvent system ethyl acetate/ethanol/triethylamine=50:2:1 gives 8.1 g (68%) of 2-(4-n-butylamino-2,2,6,6-tetramethylpiperidin-1-yl) ethanol (208) in the form of a white powder, m.p. 106°-111° C.

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