1-[(AMMONIOOXY)METHYL]-2-FLUOROBENZENE CHLORIDE

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

Procedure: Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane. After being heated for 36 h the reaction mixture was cooled the solvent removed under reduced pressure The ensuing residue was dissolved in CH2Cl2 (15 mL) the resulting solution washed with H2O (2×10 mL) then dried (MgSO4) filtered concentrated under reduced pressure The oil thus obtained

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

Procedure: A mixture of 9-chloro-1,2,3,4-tetrahydroacridine (6.18 g) and O-(2-fluorobenzyl)hydroxylamine hydrochloride (5.5 g) in 125 ml of n-propanol was heated at reflux for 20 hours. The reaction mixture was then added to an iced sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organics were washed with water and dried (saturated NaCl, MgSO4). was heated at reflux for 20 hours extracted with ethyl acetate (3×) The combined organics were washed with water dried (saturated NaCl, MgSO4)

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

Procedure: A mixture of 9-chloro-1,2,3,4-tetrahydroacridine (6.18 g) and O-(2-fluorobenzyl)hydroxylamine hydrochloride (5.5 g) in 125 ml of n-propanol was heated at reflux for 20 hours. The reaction mixture was then added to an iced sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organics were washed with water and dried (saturated NaCl, MgSO4). was heated at reflux for 20 hours extracted with ethyl acetate (3×) The combined organics were washed with water dried (saturated NaCl, MgSO4)

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

Procedure: Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane. After being heated for 36 h the reaction mixture was cooled the solvent removed under reduced pressure The ensuing residue was dissolved in CH2Cl2 (15 mL) the resulting solution washed with H2O (2×10 mL) then dried (MgSO4) filtered concentrated under reduced pressure The oil thus obtained

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

Procedure: Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane. After being heated for 36 h the reaction mixture was cooled the solvent removed under reduced pressure The ensuing residue was dissolved in CH2Cl2 (15 mL) the resulting solution washed with H2O (2×10 mL) then dried (MgSO4) filtered concentrated under reduced pressure The oil thus obtained

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

Procedure: A mixture of 9-chloro-1,2,3,4-tetrahydroacridine (6.18 g) and O-(2-fluorobenzyl)hydroxylamine hydrochloride (5.5 g) in 125 ml of n-propanol was heated at reflux for 20 hours. The reaction mixture was then added to an iced sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined organics were washed with water and dried (saturated NaCl, MgSO4). was heated at reflux for 20 hours extracted with ethyl acetate (3×) The combined organics were washed with water dried (saturated NaCl, MgSO4)