2-bromo-N-phenylpropanamide

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

Procedure: To 30 ml of acetone were added 1.06 g of 4-(4-cyanophenoxy)-phenol, 0.99 g of α-bromopropionanilide and 0.83 g of anhydrous potassium carbonate, and the mixture wask subjected to reflux for 16 hours with stirring. After the reaction mixture was cooled and separated from inorganic salts through filtration, acetone was distilled away therefrom. The residue was purified through a column-chromatography [silica gel, developed with ethyl acetate/n-hexane=1/1(V/V)] to give 1.07 g of the title compound (yield 60%), which was recrystallized from a mixed solvent of benzene-n-hexane to afford a crystal of melting point 133°-134° C. to reflux for 16 hours After the reaction mixture was cooled separated from inorganic salts through filtration, acetone was distilled away The residue was purified through a column-chromatography [silica gel

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

Procedure: To a solution/suspension of 0.66 g 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylic acid, 0.23 g 2-bromo-N-phenylpropionamide, and 0.15 g K2CO3 in 7 mL of DMF was added 0.17 g of KI. The reaction was stirred 10 minutes at room temperature, then heated in a N2 atmosphere at 70° C. overnight. The reaction was partitioned between H2O and EtOAc, and the organic extract washed with brine and dried with MgSO4. Filtration, concentration, and flash chromatography with a 10-60% EtOAc/hexanes gradient provided 0.35 g of pure product. was added 0.17 g of KI The reaction was partitioned between H2O and EtOAc the organic extract washed with brine dried with MgSO4 Filtration, concentration, and flash chromatography with a 10-60% EtOAc/hexanes gradient

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

Procedure: To 30 ml of acetone were added 1.06 g of 4-(4-cyanophenoxy)-phenol, 0.99 g of α-bromopropionanilide and 0.83 g of anhydrous potassium carbonate, and the mixture wask subjected to reflux for 16 hours with stirring. After the reaction mixture was cooled and separated from inorganic salts through filtration, acetone was distilled away therefrom. The residue was purified through a column-chromatography [silica gel, developed with ethyl acetate/n-hexane=1/1(V/V)] to give 1.07 g of the title compound (yield 60%), which was recrystallized from a mixed solvent of benzene-n-hexane to afford a crystal of melting point 133°-134° C. to reflux for 16 hours After the reaction mixture was cooled separated from inorganic salts through filtration, acetone was distilled away The residue was purified through a column-chromatography [silica gel

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

Procedure: A mixture of 3.5 g. of (-)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane (U.S. Pat. No. 4,131,611), 4.6 g. of 2-bromopropionanilide, 3.7 g. of sodium carbonate and 75 ml. of toluene is stirred and refluxed overnight. The mixture is diluted with 25 ml. of water and 5 ml. of 5 N sodium hydroxide and mixed. The alkaline aqueous layer is extracted with toluene. The toluene layers are combined, washed with water, dried, filtered and concentrated to an oil. The oil is triturated in 50 ml. of ether and filtered. The filtrate is acidified with 6 ml. of 3.55 N alcoholic hydrogen chloride and scratched and resuspended in ether repeatedly until crystalline. The solid is collected, washed with ether, dried, heated to solution in 25 ml. of acetonitrile, filtered and cooled, giving 1.2 g. of the desired product, m.p. 227°-228° C. A mixture of 3.5 g refluxed overnight The mixture is diluted with 25 ml The alkaline aqueous layer is extracted with toluene washed with water dried filtered concentrated to an oil The oil is triturated in 50 ml of ether and filtered The solid is collected washed with ether dried heated to solution in 25 ml of acetonitrile, filtered cooled giving 1.2 g

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

Procedure: To a solution/suspension of 0.66 g 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylic acid, 0.23 g 2-bromo-N-phenylpropionamide, and 0.15 g K2CO3 in 7 mL of DMF was added 0.17 g of KI. The reaction was stirred 10 minutes at room temperature, then heated in a N2 atmosphere at 70° C. overnight. The reaction was partitioned between H2O and EtOAc, and the organic extract washed with brine and dried with MgSO4. Filtration, concentration, and flash chromatography with a 10-60% EtOAc/hexanes gradient provided 0.35 g of pure product. was added 0.17 g of KI The reaction was partitioned between H2O and EtOAc the organic extract washed with brine dried with MgSO4 Filtration, concentration, and flash chromatography with a 10-60% EtOAc/hexanes gradient

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

Procedure: To 30 ml of acetone were added 1.06 g of 4-(4-cyanophenoxy)-phenol, 0.99 g of α-bromopropionanilide and 0.83 g of anhydrous potassium carbonate, and the mixture wask subjected to reflux for 16 hours with stirring. After the reaction mixture was cooled and separated from inorganic salts through filtration, acetone was distilled away therefrom. The residue was purified through a column-chromatography [silica gel, developed with ethyl acetate/n-hexane=1/1(V/V)] to give 1.07 g of the title compound (yield 60%), which was recrystallized from a mixed solvent of benzene-n-hexane to afford a crystal of melting point 133°-134° C. to reflux for 16 hours After the reaction mixture was cooled separated from inorganic salts through filtration, acetone was distilled away The residue was purified through a column-chromatography [silica gel