(2-piperazin-1-ylphenyl)methanol

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-piperazin-1-yl-phenyl)-methanol (200 mg, 1.04 mmol) was added to a suspension of 4-chloropyridine hydrochloride (225 mg, 1.50 mmol), tris[2-(2-methoxy)ethyl]amine (32 μL, 0.10 mmol), powdered potassium hydroxide (225 mg, 4.01 mmol) and potassium carbonate (275 mg, 1.99 mmol) in 10 mL of toluene. The reaction mixture was heated to 120° C. overnight. The reaction mixture was concentrated and the residue was purified by reverse phase HPLC. The material was still less than 50% pure, but was used in the next step without further purification. The reaction mixture was concentrated the residue was purified by reverse phase HPLC was used in the next step without further purification

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-piperazin-1-yl-phenyl)-methanol (200 mg, 1.04 mmol) was added to a suspension of 4-chloropyridine hydrochloride (225 mg, 1.50 mmol), tris[2-(2-methoxy)ethyl]amine (32 μL, 0.10 mmol), powdered potassium hydroxide (225 mg, 4.01 mmol) and potassium carbonate (275 mg, 1.99 mmol) in 10 mL of toluene. The reaction mixture was heated to 120° C. overnight. The reaction mixture was concentrated and the residue was purified by reverse phase HPLC. The material was still less than 50% pure, but was used in the next step without further purification. The reaction mixture was concentrated the residue was purified by reverse phase HPLC was used in the next step without further purification

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

Procedure: 2-piperazin-1-yl-benzoic acid sulfuric acid salt (˜10 mmol) was suspended in 50 mL of tetrahydrofuran. Then 100 mL of 1.0 M borane in tetrahydrofuran (100 mmol) was added and the reaction was stirred at room temperature overnight with a bubbler attached to release pressure in the flask. The reaction mixture was diluted with 50 mL of methanol. The reduced product (470 mg) crystallized out of the mixture during evaporation. The reduced product (470 mg) crystallized out of the mixture during evaporation

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-piperazin-1-yl-phenyl)-methanol (200 mg, 1.04 mmol) was added to a suspension of 4-chloropyridine hydrochloride (225 mg, 1.50 mmol), tris[2-(2-methoxy)ethyl]amine (32 μL, 0.10 mmol), powdered potassium hydroxide (225 mg, 4.01 mmol) and potassium carbonate (275 mg, 1.99 mmol) in 10 mL of toluene. The reaction mixture was heated to 120° C. overnight. The reaction mixture was concentrated and the residue was purified by reverse phase HPLC. The material was still less than 50% pure, but was used in the next step without further purification. The reaction mixture was concentrated the residue was purified by reverse phase HPLC was used in the next step without further purification

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

Procedure: 2-piperazin-1-yl-benzoic acid sulfuric acid salt (˜10 mmol) was suspended in 50 mL of tetrahydrofuran. Then 100 mL of 1.0 M borane in tetrahydrofuran (100 mmol) was added and the reaction was stirred at room temperature overnight with a bubbler attached to release pressure in the flask. The reaction mixture was diluted with 50 mL of methanol. The reduced product (470 mg) crystallized out of the mixture during evaporation. The reduced product (470 mg) crystallized out of the mixture during evaporation