2-(3-chlorophenyl)propan-2-amine

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 27.8 g (0.3 mol) of chloroacetone, 16.0 g (0.1 mol) of 3-chloro-α,α-dimethylbenzylamine and 11.2 g (0.11 mol) of triethylamine were dissolved in 200 ml of N,N-dimethylacetamide, and the mixture was heated at 80° C.. for 3 hours under stirring. The reaction solution was cooled, then poured into a large amount of water and extracted with toluene. The toluene layer was washed with water and then dried over anhydrous magensium sulfate. Then, the toluene layer was distilled off under reduced pressure to obtain 6.9 g (yield: 30.6%) of the desired compound. The reaction solution was cooled extracted with toluene The toluene layer was washed with water dried over anhydrous magensium sulfate Then, the toluene layer was distilled off under reduced pressure

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

Procedure: N-(2-Fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide (1.00 g, 2.75 mmol), 3-chlorocumylamine (0.630 g, 3.71 mmol), N-methylmorpholine (0.670 g, 6.62 mmol), and benzene (10 ml) as a solvent were placed into a round bottom flask (50 cc) and stirred overnight at room temperature, followed by heating at 50° C. for 7 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were isolated by filtration. The crystals were washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(3-chlorocumyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.859 g, 58.6% yield). by heating at 50° C. for 7 hours After completion of the reaction the solvent was distilled off under reduced pressure the precipitated crystals were isolated by filtration The crystals were washed with hexane dried

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

Procedure: N-(2-Fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide (1.00 g, 2.75 mmol), 3-chlorocumylamine (0.630 g, 3.71 mmol), N-methylmorpholine (0.670 g, 6.62 mmol), and benzene (10 ml) as a solvent were placed into a round bottom flask (50 cc) and stirred overnight at room temperature, followed by heating at 50° C. for 7 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were isolated by filtration. The crystals were washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(3-chlorocumyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.859 g, 58.6% yield). by heating at 50° C. for 7 hours After completion of the reaction the solvent was distilled off under reduced pressure the precipitated crystals were isolated by filtration The crystals were washed with hexane dried

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

Procedure: The same procedure as employed in the preparation of Example 226 (step a) but using 4-[(4-hexylphenyl)ethynyl]benzaldehyde and 1-(3-chlorophenyl)-1-methylethylamine gave the title compound as a brown oil (80%). HPLC (Condition A), Rt: 4.73 min (HPLC purity: 98.7%). The same procedure as employed in the preparation of Example 226 (step a) but

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

Procedure: The same procedure as employed in the preparation of Example 226 (step a) but using 4-[(4-hexylphenyl)ethynyl]benzaldehyde and 1-(3-chlorophenyl)-1-methylethylamine gave the title compound as a brown oil (80%). HPLC (Condition A), Rt: 4.73 min (HPLC purity: 98.7%). The same procedure as employed in the preparation of Example 226 (step a) but

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

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

Procedure: N-(2-Fluoro-4-chloro-5-cyclopentyloxyphenyl)-3,4,5,6-tetrahydroisophthalimide (1.00 g, 2.75 mmol), 3-chlorocumylamine (0.630 g, 3.71 mmol), N-methylmorpholine (0.670 g, 6.62 mmol), and benzene (10 ml) as a solvent were placed into a round bottom flask (50 cc) and stirred overnight at room temperature, followed by heating at 50° C. for 7 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were isolated by filtration. The crystals were washed with hexane and dried to obtain N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)-N'-(3-chlorocumyl)-3,4,5,6-tetrahydrophthalamide as white crystals (0.859 g, 58.6% yield). by heating at 50° C. for 7 hours After completion of the reaction the solvent was distilled off under reduced pressure the precipitated crystals were isolated by filtration The crystals were washed with hexane dried

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 15 ml of N,N-dimethylformamide were added 2.6 g of 1-methyl-1-(3-chlorophenyl)ethylamine, 2.0 g of potassium carbonate and 2.1 g of 3-chloro-2-methylpropene, and the solution was then stirred at 85° C. for 1 hour. After potassium carbonate was removed by filtration, 100 ml of water were added, followed by extraction with toluene. The resultant extract was dried over anhydrous sodium sulfate, and then concentrated by an evaporator. Afterward, silica gel column chromatography was done to obtain 2.6 g of the desired amine. After potassium carbonate was removed by filtration, 100 ml of water were added followed by extraction with toluene The resultant extract was dried over anhydrous sodium sulfate concentrated by an evaporator

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

Procedure: 1-Methyl-1-(3-chlorophenyl)ethylamine (5.0 g) was added slowly to formalin (aqueous 37% HCHO solution) (3.5 g) at room temperature. This was allowed to react as it was for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, which was then extracted with ether. After it was washed with saturated saline, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the captioned compound (5.6 g) as syrup. to react as it was then extracted with ether After it was washed with saturated saline the organic layer was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 27.8 g (0.3 mol) of chloroacetone, 16.0 g (0.1 mol) of 3-chloro-α,α-dimethylbenzylamine and 11.2 g (0.11 mol) of triethylamine were dissolved in 200 ml of N,N-dimethylacetamide, and the mixture was heated at 80° C. for 3 hours under stirring. The reaction solution was cooled, then poured into a large amount of water and extracted with toluene. The toluene layer was washed with water and then dried over anhydrous magensium sulfate. Then, the toluene layer was distilled off under reduced pressure to obtain 6.9 g (yield: 30.6%) of the desired compound. The reaction solution was cooled extracted with toluene The toluene layer was washed with water dried over anhydrous magensium sulfate Then, the toluene layer was distilled off under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 27.8 g (0.3 mol) of chloroacetone, 16.0 g (0.1 mol) of 3-chloro-α,α-dimethylbenzylamine and 11.2 g (0.11 mol) of triethylamine were dissolved in 200 ml of N,N-dimethylacetamide, and the mixture was heated at 80° C.. for 3 hours under stirring. The reaction solution was cooled, then poured into a large amount of water and extracted with toluene. The toluene layer was washed with water and then dried over anhydrous magensium sulfate. Then, the toluene layer was distilled off under reduced pressure to obtain 6.9 g (yield: 30.6%) of the desired compound. The reaction solution was cooled extracted with toluene The toluene layer was washed with water dried over anhydrous magensium sulfate Then, the toluene layer was distilled off under reduced pressure