1-[(4-chlorophenyl)methyl]piperidin-4-one

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

Procedure: Dissolve 1-(4-chlorobenzyl)-4-piperidone (0.0456 mmol), hydroxylamine hydrochloride (0.0456 mmol) and sodium acetate (0.0456 mmol) in aqueous ethanol (450 mL). Stir approximately 30 minutes to 2 hours while warming. Add methylene chloride (450 mL), separate the organic phase, and extract the aqueous phase with methylene chloride (100 mL). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound. while warming Add methylene chloride (450 mL), separate the organic phase extract the aqueous phase with methylene chloride (100 mL) Combine the organic phases and dry (MgSO4) Evaporate the solvent in vacuo

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

Procedure: Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound. heat to reflux reflux for 4 hours Filter the hot suspension wash the residue with hot acetone (4×20 mL) evaporate the solvent in vacuo

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

Procedure: Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound. heat to reflux reflux for 4 hours Filter the hot suspension wash the residue with hot acetone (4×20 mL) evaporate the solvent in vacuo

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

Procedure: Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound. heat to reflux reflux for 4 hours Filter the hot suspension wash the residue with hot acetone (4×20 mL) evaporate the solvent in vacuo

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

Procedure: Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound. heat to reflux reflux for 4 hours Filter the hot suspension wash the residue with hot acetone (4×20 mL) evaporate the solvent in vacuo

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

Procedure: To a solution of 4-piperidine trifluoroacetate obtained from step (iv) (853 mg, 4.0 mmol) in DMF was added triethylamine (2.66 mL, 19.2 mmol), followed by 4-chlorobenzyl chloride (753 mg, 4.8 mmol) and the reaction mixture was stirred overnight at room temperature. The volatiles were removed in vacuo, residue was dissolved in ethylacetate, washed with water (H2O), organic layer was dried over sodium sulphate (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash chromatography to give the subtitled compound (350 mg). The volatiles were removed in vacuo, residue was dissolved in ethylacetate washed with water (H2O), organic layer was dried over sodium sulphate (Na2SO4) filtered concentrated The residue was purified by silica gel flash chromatography

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

Procedure: Dissolve 1-(4-chlorobenzyl)-4-piperidone (0.0456 mmol), hydroxylamine hydrochloride (0.0456 mmol) and sodium acetate (0.0456 mmol) in aqueous ethanol (450 mL). Stir approximately 30 minutes to 2 hours while warming. Add methylene chloride (450 mL), separate the organic phase, and extract the aqueous phase with methylene chloride (100 mL). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound. while warming Add methylene chloride (450 mL), separate the organic phase extract the aqueous phase with methylene chloride (100 mL) Combine the organic phases and dry (MgSO4) Evaporate the solvent in vacuo

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

Procedure: Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound. heat to reflux reflux for 4 hours Filter the hot suspension wash the residue with hot acetone (4×20 mL) evaporate the solvent in vacuo

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

Procedure: Dissolve 4-piperidone (17 mmol) in 3-pentanone (25 mL) and heat to reflux. Add cesium carbonate (19 mmol) and a catalytic amount of potassium iodide, followed by 4-chlorobenzyl chloride (20 mmol). Stir and reflux for 4 hours. Filter the hot suspension, wash the residue with hot acetone (4×20 mL), combine the filtrate and washings, and evaporate the solvent in vacuo to give the title compound. heat to reflux reflux for 4 hours Filter the hot suspension wash the residue with hot acetone (4×20 mL) evaporate the solvent in vacuo

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

Procedure: To a solution of 4-piperidine trifluoroacetate obtained from step (iv) (853 mg, 4.0 mmol) in DMF was added triethylamine (2.66 mL, 19.2 mmol), followed by 4-chlorobenzyl chloride (753 mg, 4.8 mmol) and the reaction mixture was stirred overnight at room temperature. The volatiles were removed in vacuo, residue was dissolved in ethylacetate, washed with water (H2O), organic layer was dried over sodium sulphate (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash chromatography to give the subtitled compound (350 mg). The volatiles were removed in vacuo, residue was dissolved in ethylacetate washed with water (H2O), organic layer was dried over sodium sulphate (Na2SO4) filtered concentrated The residue was purified by silica gel flash chromatography