1-benzyl-2-(chloromethyl)piperidine

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

Procedure: To a stirred solution of compound 13 (3.6 g, 15.00 mmol) in chloroform (50 mL) was added thionyl chloride (1.34 mL) at 0° C. The reaction mixture was heated at reflux for 2 hours and then concentrated. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane to provide compound 14 as an oil. The reaction mixture was heated at reflux for 2 hours concentrated The residue was dissolved in EtOAc washed with saturated sodium bicarbonate solution, water and brine The organic layer was dried over Na2SO4 filtered concentrated The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane

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

Procedure: To a stirred solution of compound 13 (3.6 g, 15.00 mmol) in chloroform (50 mL) was added thionyl chloride (1.34 mL) at 0° C. The reaction mixture was heated at reflux for 2 hours and then concentrated. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane to provide compound 14 as an oil. The reaction mixture was heated at reflux for 2 hours concentrated The residue was dissolved in EtOAc washed with saturated sodium bicarbonate solution, water and brine The organic layer was dried over Na2SO4 filtered concentrated The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane

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

Procedure: To a stirred solution of compound 13 (3.6 g, 15.00 mmol) in chloroform (50 mL) was added thionyl chloride (1.34 mL) at 0° C. The reaction mixture was heated at reflux for 2 hours and then concentrated. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane to provide compound 14 as an oil. The reaction mixture was heated at reflux for 2 hours concentrated The residue was dissolved in EtOAc washed with saturated sodium bicarbonate solution, water and brine The organic layer was dried over Na2SO4 filtered concentrated The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane