2-(3-bromophenyl)-N,N-dimethylacetamide

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane in tetrahydrofuran (1.0M, 24.7 ml) was added dropwise to a tetrahydrofuran solution of 2-(3-bromophenyl)-N,N-dimethyl-acetamide (1.5 g, Example 25a)) at 0° C. Once addition was complete the solution was refluxed at 90° C. for 20 hours. The solution was cooled to room temperature, acidified with hydrochloric acid (6M, 10 ml) and refluxed for a further hour. The solution was cooled to room temperature and extracted with diethyl ether. The aqueous layer was basified with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was converted to the hydrochloride salt by treatment with a solution of 4M hydrogen chloride in dioxan to give the sub-title compound as a hygroscopic gum (0.949 g). Once addition The solution was cooled to room temperature refluxed for a further hour The solution was cooled to room temperature extracted with diethyl ether extracted with ethyl acetate The extracts were dried over anhydrous magnesium sulfate filtered concentrated

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

Procedure: Prepared according to the method described in Example 24a) from 1-(3-is dimethylaminopropyl)-3-ethylcarbodiimide 4-hydrochloride (2.15 g), 4-dimethylaminopyridine (3.82 g), a 2M solution of dimethylamine in tetrahydrofuran (10 ml) and a solution of 3-bromophenylacetic acid (2.15 g) in dichloromethane (100 ml). The mixture was stirred overnight at room temperature. The reaction mixture was washed with 2M hydrochloric acid (3×100 ml), the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The sub-title compound was obtained as an oil (2.89 g). Prepared The reaction mixture was washed with 2M hydrochloric acid (3×100 ml) the organic layer was dried over anhydrous magnesium sulfate filtered concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane in tetrahydrofuran (1.0M, 24.7 ml) was added dropwise to a tetrahydrofuran solution of 2-(3-bromophenyl)-N,N-dimethyl-acetamide (1.5 g, Example 25a)) at 0° C. Once addition was complete the solution was refluxed at 90° C. for 20 hours. The solution was cooled to room temperature, acidified with hydrochloric acid (6M, 10 ml) and refluxed for a further hour. The solution was cooled to room temperature and extracted with diethyl ether. The aqueous layer was basified with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was converted to the hydrochloride salt by treatment with a solution of 4M hydrogen chloride in dioxan to give the sub-title compound as a hygroscopic gum (0.949 g). Once addition The solution was cooled to room temperature refluxed for a further hour The solution was cooled to room temperature extracted with diethyl ether extracted with ethyl acetate The extracts were dried over anhydrous magnesium sulfate filtered concentrated

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

Procedure: Prepared according to the method described in Example 24a) from 1-(3-is dimethylaminopropyl)-3-ethylcarbodiimide 4-hydrochloride (2.15 g), 4-dimethylaminopyridine (3.82 g), a 2M solution of dimethylamine in tetrahydrofuran (10 ml) and a solution of 3-bromophenylacetic acid (2.15 g) in dichloromethane (100 ml). The mixture was stirred overnight at room temperature. The reaction mixture was washed with 2M hydrochloric acid (3×100 ml), the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The sub-title compound was obtained as an oil (2.89 g). Prepared The reaction mixture was washed with 2M hydrochloric acid (3×100 ml) the organic layer was dried over anhydrous magnesium sulfate filtered concentrated

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

Procedure: Prepared according to the method described in Example 24a) from 1-(3-is dimethylaminopropyl)-3-ethylcarbodiimide 4-hydrochloride (2.15 g), 4-dimethylaminopyridine (3.82 g), a 2M solution of dimethylamine in tetrahydrofuran (10 ml) and a solution of 3-bromophenylacetic acid (2.15 g) in dichloromethane (100 ml). The mixture was stirred overnight at room temperature. The reaction mixture was washed with 2M hydrochloric acid (3×100 ml), the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The sub-title compound was obtained as an oil (2.89 g). Prepared The reaction mixture was washed with 2M hydrochloric acid (3×100 ml) the organic layer was dried over anhydrous magnesium sulfate filtered concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane in tetrahydrofuran (1.0M, 24.7 ml) was added dropwise to a tetrahydrofuran solution of 2-(3-bromophenyl)-N,N-dimethyl-acetamide (1.5 g, Example 25a)) at 0° C. Once addition was complete the solution was refluxed at 90° C. for 20 hours. The solution was cooled to room temperature, acidified with hydrochloric acid (6M, 10 ml) and refluxed for a further hour. The solution was cooled to room temperature and extracted with diethyl ether. The aqueous layer was basified with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was converted to the hydrochloride salt by treatment with a solution of 4M hydrogen chloride in dioxan to give the sub-title compound as a hygroscopic gum (0.949 g). Once addition The solution was cooled to room temperature refluxed for a further hour The solution was cooled to room temperature extracted with diethyl ether extracted with ethyl acetate The extracts were dried over anhydrous magnesium sulfate filtered concentrated

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

Procedure: Prepared according to the method described in Example 24a) from 1-(3-is dimethylaminopropyl)-3-ethylcarbodiimide 4-hydrochloride (2.15 g), 4-dimethylaminopyridine (3.82 g), a 2M solution of dimethylamine in tetrahydrofuran (10 ml) and a solution of 3-bromophenylacetic acid (2.15 g) in dichloromethane (100 ml). The mixture was stirred overnight at room temperature. The reaction mixture was washed with 2M hydrochloric acid (3×100 ml), the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The sub-title compound was obtained as an oil (2.89 g). Prepared The reaction mixture was washed with 2M hydrochloric acid (3×100 ml) the organic layer was dried over anhydrous magnesium sulfate filtered concentrated