N-(1,3-diphenylpropan-2-ylidene)hydroxylamine

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

Procedure: A mixture of the above oxime (3.0 g, 13 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (4.6 g, 13 mmol), potassium carbonate (5.4 g, 39 mmol) and acetone (40 ml) was stirred at room temperature for 3 days. The mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The residue was purified by column chromatography on silica gel (50 g, cyclohexane/ethyl acetate 3/1) to give 1.8 g of (R)-1-(2-(((1,3-diphenylpropan-2-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester. The mixture was filtered the solvent was evaporated from the filtrate in vacuo The residue was purified by column chromatography on silica gel (50 g, cyclohexane/ethyl acetate 3/1)

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

Procedure: To a solution of 1,3-diphenyl-2-propanone (5.0 g, 24 mmol) and hydroxylammonium chloride (3.3 g, 48 mmol) in a mixture of absolute ethanol (30 ml) and water (10 ml) was carefully added a solution of sodium carbonate (13.2 g, 96 mmol) in water (30 ml). The resulting mixture was stirred at room temperature for 16 h. The precipitated compound was collected and washed with water (3×15 ml) and dried to give 4.9 g of 1,3-diphenyl-2-propanone oxime. The precipitated compound was collected washed with water (3×15 ml) dried

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

Procedure: To a solution of 1,3-diphenyl-2-propanone (5.0 g, 24 mmol) and hydroxylammonium chloride (3.3 g, 48 mmol) in a mixture of absolute ethanol (30 ml) and water (10 ml) was carefully added a solution of sodium carbonate (13.2 g, 96 mmol) in water (30 ml). The resulting mixture was stirred at room temperature for 16 h. The precipitated compound was collected and washed with water (3×15 ml) and dried to give 4.9 g of 1,3-diphenyl-2-propanone oxime. The precipitated compound was collected washed with water (3×15 ml) dried

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

Procedure: A mixture of the above oxime (3.0 g, 13 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (4.6 g, 13 mmol), potassium carbonate (5.4 g, 39 mmol) and acetone (40 ml) was stirred at room temperature for 3 days. The mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The residue was purified by column chromatography on silica gel (50 g, cyclohexane/ethyl acetate 3/1) to give 1.8 g of (R)-1-(2-(((1,3-diphenylpropan-2-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester. The mixture was filtered the solvent was evaporated from the filtrate in vacuo The residue was purified by column chromatography on silica gel (50 g, cyclohexane/ethyl acetate 3/1)

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

Procedure: To a solution of 1,3-diphenyl-2-propanone (5.0 g, 24 mmol) and hydroxylammonium chloride (3.3 g, 48 mmol) in a mixture of absolute ethanol (30 ml) and water (10 ml) was carefully added a solution of sodium carbonate (13.2 g, 96 mmol) in water (30 ml). The resulting mixture was stirred at room temperature for 16 h. The precipitated compound was collected and washed with water (3×15 ml) and dried to give 4.9 g of 1,3-diphenyl-2-propanone oxime. The precipitated compound was collected washed with water (3×15 ml) dried