1-(3-chloropropoxy)-2-fluorobenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Prepared by Procedure G and Scheme B1 using 1-(3-chloropropoxy)-2-fluorobenzene and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 399.2 (M+H)+. Prepared by Procedure G and Scheme B1

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

Procedure: Prepared by Procedure U and Scheme AK using 2-fluorophenol and 1-bromo-3-chloropropane. Prepared by Procedure U and Scheme AK

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

Procedure: To a solution of 0.58 g (1.5 mM) of N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 1.0 ml (7.5 mM) of triethylamine in ethanol were added 0.37 g (2.0 mM) of 3-(2-fluorophenoxy)-propyl chloride and 0.28 g (1.9 mM) of sodium iodide at room temperature and the mixture was refluxed under nitrogen for 20 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The resulting crude product was purified by column chromatography (methanol/ethyl acetate 30-50%) to provide the title compound. the mixture was refluxed under nitrogen for 20 hours The solvent was then distilled off under reduced pressure the residue was diluted with water extracted with chloroform The organic layer was washed with saturated aqueous solution of sodium chloride dried over MgSO4 The resulting crude product was purified by column chromatography (methanol/ethyl acetate 30-50%)

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

Procedure: Prepared by Procedure G and Scheme B1 using 1-(3-chloropropoxy)-2-fluorobenzene and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 399.2 (M+H)+. Prepared by Procedure G and Scheme B1

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

Procedure: Prepared by Procedure U and Scheme AK using 2-fluorophenol and 1-bromo-3-chloropropane. Prepared by Procedure U and Scheme AK

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

Procedure: A mixture of 5.85 g (0.02 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine, 3.76 g (0.02 mole) of 2-(3-chloropropoxy)-1-fluorobenzene, and sodium carbonate (4.80 g, 0.045 mole) in 300 ml of 1-butanol containing 0.3 g of potassium iodide was heated overnight at gentle reflux. The reaction mixture was stripped to dryness and the resulting oil partitioned between chloroform-5% sodium hydroxide and then between chloroform-water. Removal of chloroform gave an oil which was converted to the oxalate salt. The salt was recrystallized from methanol-diethyl ether. The salt was subsequently triturated with isopropanol, and was dried overnight at 80° C. to give 5.82 g (55%) of product, m.p. 182°-183° C. was heated overnight at gentle reflux the resulting oil partitioned between chloroform-5% sodium hydroxide Removal of chloroform gave an oil which The salt was recrystallized from methanol-diethyl ether The salt was subsequently triturated with isopropanol was dried overnight at 80° C.