(NZ)-N-(2-phenylcyclohex-2-en-1-ylidene)hydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of the above oxime (0.55 g, 2.9 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (1.0 g, 2.9 mmol, EP 374801A), potassium carbonate (1.0 g, 7.3 mmol) and acetone (25 ml) was stirred at ambient temperature for 14 days. The mixture was filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel (125 g, heptane/ethyl acetate=1/1) to give 0.4 g of (R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil. The mixture was filtered the solvent evaporated in vacuo The residue was purified by column chromatography on silica gel (125 g, heptane/ethyl acetate=1/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-2-cyclohexen-1-one (0.6 g, 3.5 mmol, Tetrahedron 1972, 28, 2369), hydroxylammonium chloride (0.5 g, 7 mmol) and dry pyridine (15 ml) was heated at reflux for 3 h. The reaction mixture was allowed to cool and the solvent was evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water. A 10% citric acid solution was added until acidic pH and the phases were separated. The organic phase was extracted with a 10% citric acid solution and dried (MgSO4). The solvent was evaporated in vacuo to give 0.55 g of 2-phenyl-2-cyclohexen-1 -one oxime. M.p. 144°-146° C. was heated at reflux for 3 h to cool the solvent was evaporated in vacuo The residue was dissolved in a mixture of ethyl acetate and water A 10% citric acid solution was added until acidic pH the phases were separated The organic phase was extracted with a 10% citric acid solution dried (MgSO4) The solvent was evaporated in vacuo