1-(4-aminophenyl)propan-2-one

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

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

Procedure: N-Chlorosuccinamide (1.79 g, 13.4 mmol) is added to a stirred solution of 1-(4-amino-phenyl)-propan-2-one (2.0 g, 13.4 mmol) in chloroform at 0° C. After 1 hour the reaction is complete. The solvent is removed to give the title compound. The solvent is removed

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

Procedure: N-Chlorosuccinamide (1.79 g, 13.4 mmol) is added to a stirred solution of 1-(4-amino-phenyl)-propan-2-one (2.0 g, 13.4 mmol) in chloroform at 0° C. After 1 hour the reaction is complete. The solvent is removed to give the title compound. The solvent is removed

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

Procedure: 1-(4-nitro-phenyl)-propan-2-one (150 mg) was dissolved in methanol (5 ml) and then Pd/C (50 mg) was added. The resulting reaction mixture was stirred for 10 hr at room temperature under hydrogen pressure. The reaction mixture was filtered over celite and the filtrate evaporated. Purification by column chromatography over silica gel using ethyl acetate and hexane (1:9) as eluent gave 1-(4-amino-phenyl)-propan-2-one (60 mg, 48%). The resulting reaction mixture The reaction mixture was filtered over celite the filtrate evaporated Purification by column chromatography over silica gel

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

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

Procedure: To a solution of 1-(4-aminophenyl)acetone (1.13 g, 7.57 mmol) and pyridine (1.84 ml, 22.7 mmol) in tetrahydrofuran (50 ml) was added 2,2,2-trichloroethyl chloroformate (1.57 ml, 11.4 mmol) with ice-cooling, and the mixture was stirred for 1 hour with ice-cooling and then at room temperature for 1 hour, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1) to obtain the desired product (1.44 g, 58.4%) as an oil. cooling cooling at room temperature for 1 hour the mixture was extracted with ethyl acetate The extract was washed with water dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1)

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

Procedure: A solution of 1-(4-nitrophenyl)acetone (2.00 g, 11.2 mmol), 10% palladium-carbon (200 mg), methanol (20 ml) and tetrahydrofuran (10 ml) was stirred under a hydrogen atmosphere for 12 hours. Insolubles were filtered off to obtain the desired product (1.13 g, 67.6%) as an oil. Insolubles were filtered off

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

Procedure: Following general procedure B1, 4-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.140 g, 0.53 mmol) was reacted with 1-(4-aminophenyl)propan-2-one (0.094 g, 0.63 mmol) to afford the title compound (0.119 g, 60%) as a light yellow solid. MW=377.87. 1H NMR (DMSO-d6, 500 MHz) δ 8.84 (s, 1H), 8.29-8.22 (m, 2H), 7.75 (d, J=8.5 Hz, 2H), 7.55-7.48 (m, 2H), 7.20 (d, J=8.5 Hz, 2H), 3.74 (s, 2H), 2.94-2.84 (m, 4H), 2.15 (s, 3H), 2.14-2.06 (m, 2H); APCI MS m/z 378 [M+H]+.

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

Procedure: To a solution of 1-(4-nitrophenyl)propan-2-one (0.650 g, 3.63 mmol) in ethanol (20 mL) was added 10% palladium on carbon (0.060 g) and the mixture stirred at rt under 1 atm of H2 for 1 h. After this time, the mixture was filtered over celite, concentrated, and the residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.280 g, 51%) as an orange oil. MW=149.19. 1H NMR (CDCl3, 500 MHz) δ 7.00-6.96 (m, 2H), 6.68-6.63 (m, 2H), 3.63 (s, 2H), 3.56 (s, 2H), 2.11 (s, 3H); APCI MS m/z 150 [M+H]+. After this time, the mixture was filtered over celite, concentrated the residue was purified by column chromatography (silica, hexanes/ethyl acetate)

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

Procedure: N-Chlorosuccinamide (1.79 g, 13.4 mmol) is added to a stirred solution of 1-(4-amino-phenyl)-propan-2-one (2.0 g, 13.4 mmol) in chloroform at 0° C. After 1 hour the reaction is complete. The solvent is removed to give the title compound. The solvent is removed

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

Procedure: 1-(4-nitro-phenyl)-propan-2-one (150 mg) was dissolved in methanol (5 ml) and then Pd/C (50 mg) was added. The resulting reaction mixture was stirred for 10 hr at room temperature under hydrogen pressure. The reaction mixture was filtered over celite and the filtrate evaporated. Purification by column chromatography over silica gel using ethyl acetate and hexane (1:9) as eluent gave 1-(4-amino-phenyl)-propan-2-one (60 mg, 48%). The resulting reaction mixture The reaction mixture was filtered over celite the filtrate evaporated Purification by column chromatography over silica gel