N-[1-[(4-chlorophenyl)methyl]piperidin-4-ylidene]hydroxylamine

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

Procedure: Add 1-(4-chlorobenzyl)-4-piperidone oxime (1.87 mmol) to a solution of lithium aluminum hydride (2.5 mL of a 1M solution in tetrahydrofuran) and place under a nitrogen atmosphere. Heat at reflux for 2 hours, cool and pour into dilute aqueous sodium hydroxide. Extract with a mixture of ethyl ether/ethyl acetate (2×), wash with aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound. Heat at reflux for 2 hours cool Extract with a mixture of ethyl ether/ethyl acetate (2×) wash with aqueous sodium chloride dry (MgSO4) Evaporate the solvent in vacuo

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: Add 1-(4-chlorobenzyl)-4-piperidone oxime (1.87 mmol) to a solution of lithium aluminum hydride (2.5 mL of a 1 M solution in tetrahydrofuran) and place under a nitrogen atmosphere. Heat at reflux for 2 hours, cool and pour into dilute aqueous sodium hydroxide. Extract with a mixture of ethyl ether/ethyl acetate (2×), wash with aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound. Heat at reflux for 2 hours cool Extract with a mixture of ethyl ether/ethyl acetate (2×) wash with aqueous sodium chloride dry (MgSO4) Evaporate the solvent in vacuo

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

Procedure: Add 1-(4-chlorobenzyl)-4-piperidone oxime (1.87 mmol) to a solution of lithium aluminum hydride (2.5 mL of a 1M solution in tetrahydrofuran) and place under a nitrogen atmosphere. Heat at reflux for 2 hours, cool and pour into dilute aqueous sodium hydroxide. Extract with a mixture of ethyl ether/ethyl acetate (2×), wash with aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound. Heat at reflux for 2 hours cool Extract with a mixture of ethyl ether/ethyl acetate (2×) wash with aqueous sodium chloride dry (MgSO4) Evaporate the solvent in vacuo

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: Add 1-(4-chlorobenzyl)-4-piperidone oxime (1.87 mmol) to a solution of lithium aluminum hydride (2.5 mL of a 1 M solution in tetrahydrofuran) and place under a nitrogen atmosphere. Heat at reflux for 2 hours, cool and pour into dilute aqueous sodium hydroxide. Extract with a mixture of ethyl ether/ethyl acetate (2×), wash with aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound. Heat at reflux for 2 hours cool Extract with a mixture of ethyl ether/ethyl acetate (2×) wash with aqueous sodium chloride dry (MgSO4) Evaporate the solvent in vacuo