Hydroxylamine → N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-ylidene]hydroxylamine

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Reaction Steps

2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-4-oxopiperidine prepared according to DE 199 09 767 A1 is dissolved in methanol containing 10% by weight of KOH and stirred for 5 hours at room temperature. Methanol is evaporated, the residue is washed with water and dried in vacuo. A solution of 95.24 g (0.3 mol) of 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-4-oxopiperidine and 29.7 g (0.45 mol) 50% aqueous hydroxylamine solution in 150 ml of methanol is stirred under reflux during 5 h. The suspension is then cooled to −8° C. and filtered. The solid is washed with 100 ml of a cold (−20° C.) methanol and dried to afford 64 g (64.1%) of the title compound as a white, microcrystalline powder, mp 130-145 oC. C20H32N2O2 (332.49) calculated C 72.25%, H 9.70%, N 8.43%; found 72.19% C, 9.54% H, 8.43% N.

Provenance & Evidence