1-(4-chlorobutyl)-4-fluorobenzene

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

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

Procedure: A mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (1.4 g; 0.0058 mol), potassium carbonate (4 g; 0.0029 mol), a catalytic amount of potassium iodide (0.030 g) and compound of Description 9 [1-(4-chloro-butyl)-4-fluoro-benzene] (5.4 g; 0.029 mol) in dimethylformamide (40 ml) was heated at 80° C. for 6 hours. The reaction mixture was cool down to room temperature. quenched with water and then extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5), the desired compound was obtained as an oil. A solution of this oil in methanol was saturated with gaseous hydrogen chloride. A solid was precipitated. The title compound hydrochloride was collected by filtration, washed with hexane and dried under vacuum (0.66 g). quenched with water extracted with ethyl acetate The organic extract was dried (MgSO4) evaporated under vacuum After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5)

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

Procedure: Triethylsilane (22.5 ml; 0.141 mol) was added dropwise to a cold (~0° C.) stirring mixture of 4-chloro-4'-fluoro-butyrophenone (10 ml; 0.0613 mol) in trifluoroacetic acid (47 ml). The reaction mixture was stirred at room temperature under nitrogen for 6 hours. The reaction was quenched with brine and extracted with diethyl ether. The organic extract was dried (MgSO4) and evaporated under vacuum giving the desired compound as an oil. The reaction mixture was stirred at room temperature under nitrogen for 6 hours The reaction was quenched with brine extracted with diethyl ether The organic extract was dried (MgSO4) evaporated under vacuum

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

Procedure: A mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (1.4 g; 0.0058 mol), potassium carbonate (4 g; 0.0029 mol), a catalytic amount of potassium iodide (0.030 g) and compound of Description 9 [1-(4-chloro-butyl)-4-fluoro-benzene] (5.4 g; 0.029 mol) in dimethylformamide (40 ml) was heated at 80° C. for 6 hours. The reaction mixture was cool down to room temperature. quenched with water and then extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5), the desired compound was obtained as an oil. A solution of this oil in methanol was saturated with gaseous hydrogen chloride. A solid was precipitated. The title compound hydrochloride was collected by filtration, washed with hexane and dried under vacuum (0.66 g). quenched with water extracted with ethyl acetate The organic extract was dried (MgSO4) evaporated under vacuum After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5)

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

Procedure: A mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (1.4 g; 0.0058 mol), potassium carbonate (4 g; 0.0029 mol), a catalytic amount of potassium iodide (0.030 g) and compound of Description 9 [1-(4-chloro-butyl)-4-fluoro-benzene] (5.4 g; 0.029 mol) in dimethylformamide (40 ml) was heated at 80° C. for 6 hours. The reaction mixture was cool down to room temperature. quenched with water and then extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5), the desired compound was obtained as an oil. A solution of this oil in methanol was saturated with gaseous hydrogen chloride. A solid was precipitated. The title compound hydrochloride was collected by filtration, washed with hexane and dried under vacuum (0.66 g). quenched with water extracted with ethyl acetate The organic extract was dried (MgSO4) evaporated under vacuum After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5)

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

Procedure: Triethylsilane (22.5 ml; 0.141 mol) was added dropwise to a cold (~0° C.) stirring mixture of 4-chloro-4'-fluoro-butyrophenone (10 ml; 0.0613 mol) in trifluoroacetic acid (47 ml). The reaction mixture was stirred at room temperature under nitrogen for 6 hours. The reaction was quenched with brine and extracted with diethyl ether. The organic extract was dried (MgSO4) and evaporated under vacuum giving the desired compound as an oil. The reaction mixture was stirred at room temperature under nitrogen for 6 hours The reaction was quenched with brine extracted with diethyl ether The organic extract was dried (MgSO4) evaporated under vacuum

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

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

Procedure: A mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (1.4 g; 0.0058 mol), potassium carbonate (4 g; 0.0029 mol), a catalytic amount of potassium iodide (0.030 g) and compound of Description 9 [1-(4-chloro-butyl)-4-fluoro-benzene] (5.4 g; 0.029 mol) in dimethylformamide (40 ml) was heated at 80° C. for 6 hours. The reaction mixture was cool down to room temperature. quenched with water and then extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5), the desired compound was obtained as an oil. A solution of this oil in methanol was saturated with gaseous hydrogen chloride. A solid was precipitated. The title compound hydrochloride was collected by filtration, washed with hexane and dried under vacuum (0.66 g). quenched with water extracted with ethyl acetate The organic extract was dried (MgSO4) evaporated under vacuum After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5)

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

Procedure: Triethylsilane (22.5 ml; 0.141 mol) was added dropwise to a cold (~0° C.) stirring mixture of 4-chloro-4'-fluoro-butyrophenone (10 ml; 0.0613 mol) in trifluoroacetic acid (47 ml). The reaction mixture was stirred at room temperature under nitrogen for 6 hours. The reaction was quenched with brine and extracted with diethyl ether. The organic extract was dried (MgSO4) and evaporated under vacuum giving the desired compound as an oil. The reaction mixture was stirred at room temperature under nitrogen for 6 hours The reaction was quenched with brine extracted with diethyl ether The organic extract was dried (MgSO4) evaporated under vacuum