N-(2-bromoethyl)-4-fluorobenzamide

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

Procedure: 4-fluoro-benzoyl chloride (3 ml; 0.026 mol) was added dropwise to a cold (~0° C.). Stirring mixture of 2-bromo-ethyl-amine hydrobromide (5 g; 0.0236 mol) and 10% aqueous sodium hydroxide (21 ml; 0.052 mol). Crystalline product started to precipitate out of the reaction mixture almost immediately. After 15 minutes of stirring, the product was collected by filtration, triturated with diethyl ether and dried under vacuum giving the desired compound as a white solid (4 g). to precipitate out of the reaction mixture almost immediately After 15 minutes of stirring the product was collected by filtration triturated with diethyl ether dried under vacuum

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

Procedure: The product from Example 48 (0.310 g) was treated with 0.34 g 2-bromo-1-(4-fluorobenzamido)ethane as described as described in Example 7 to yield 0.170 g of the desired product as a white solid, mp: 242-4° C. NMR (d6DMSO) δ 1.95 (m, 2H), 2.29 (m, 2H), 2.45-2.75 (m, 2H), 2.82 (m, 2H), 3.05-3.45 (m, 4H), 3.60-3.90 (m, 2H), 3.77 (s, 3H), 6.80 (d, 1H), 6.87 (d, 1H), 7.13 (t, 1H), 7.31 (m, 2H), 8.00 (m, 2H), 8.98 (m, 1H).

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

Procedure: 4-fluoro-benzoyl chloride (3 ml; 0.026 mol) was added dropwise to a cold (~0° C.). Stirring mixture of 2-bromo-ethyl-amine hydrobromide (5 g; 0.0236 mol) and 10% aqueous sodium hydroxide (21 ml; 0.052 mol). Crystalline product started to precipitate out of the reaction mixture almost immediately. After 15 minutes of stirring, the product was collected by filtration, triturated with diethyl ether and dried under vacuum giving the desired compound as a white solid (4 g). to precipitate out of the reaction mixture almost immediately After 15 minutes of stirring the product was collected by filtration triturated with diethyl ether dried under vacuum

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension containing 0.23 mol of-bromoethylamine hydrobromide in 200 ml of chloroform, stirred at 5° C., is added dropwise a solution containing 0.21 mol of 4-fluorobenzoyl chloride in 50 ml of chloroform, followed by a solution containing 0.46 mol of triethylamine in 100 ml of chloroform. The mixture is then stirred at room temperature for 1 hour and then at reflux for 4 hours. After cooling and evaporation of the solvent, the residue is taken up in 200 ml of ether. After filtration of the salts and concentration of the solvent, the expected product is obtained by purification of the residue by chromatography on a column of silica, using a dichloromethane/acetone (98/2) mixture as eluent. is added dropwise a solution The mixture is then stirred at room temperature for 1 hour at reflux for 4 hours After cooling evaporation of the solvent After filtration of the salts and concentration of the solvent

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

Procedure: The product from Example 48 (0.310 g) was treated with 0.34 g 2-bromo-1-(4-fluorobenzamido)ethane as described as described in Example 7 to yield 0.170 g of the desired product as a white solid, mp: 242-4° C. NMR (d6DMSO) δ 1.95 (m, 2H), 2.29 (m, 2H), 2.45-2.75 (m, 2H), 2.82 (m, 2H), 3.05-3.45 (m, 4H), 3.60-3.90 (m, 2H), 3.77 (s, 3H), 6.80 (d, 1H), 6.87 (d, 1H), 7.13 (t, 1H), 7.31 (m, 2H), 8.00 (m, 2H), 8.98 (m, 1H).

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

Procedure: 4-fluoro-benzoyl chloride (3 ml; 0.026 mol) was added dropwise to a cold (~0° C.). Stirring mixture of 2-bromo-ethyl-amine hydrobromide (5 g; 0.0236 mol) and 10% aqueous sodium hydroxide (21 ml; 0.052 mol). Crystalline product started to precipitate out of the reaction mixture almost immediately. After 15 minutes of stirring, the product was collected by filtration, triturated with diethyl ether and dried under vacuum giving the desired compound as a white solid (4 g). to precipitate out of the reaction mixture almost immediately After 15 minutes of stirring the product was collected by filtration triturated with diethyl ether dried under vacuum