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

Participants

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° C. 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