1-[(2-chlorophenyl)methyl]piperazine

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

Procedure: To a mixture of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.39 g, 0.81 mmol) and sodium triacetoxyborohydride (0.322 g, 1.52 mmol) in 1,2-dichloroethane (5 ml) at rt was added 1-(2-chloro-benzyl)-piperazine (0.20 g, 0.95 mmol). The reaction was stirred for 8 h and then washed with a saturated solution of NaHCO3, H2O, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by chromatography provided 1-{4-[4-(2-chloro-benzyl)-piperazin-1-ylmethyl]-benzyl}-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (90 mg, 19%). HPLC-MS 598 [M+1]+, 300. washed with a saturated solution of NaHCO3, H2O dried (Na2SO4) filtered concentrated under reduced pressure Purification by chromatography

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

Procedure: To a mixture of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.39 g, 0.81 mmol) and sodium triacetoxyborohydride (0.322 g, 1.52 mmol) in 1,2-dichloroethane (5 ml) at rt was added 1-(2-chloro-benzyl)-piperazine (0.20 g, 0.95 mmol). The reaction was stirred for 8 h and then washed with a saturated solution of NaHCO3, H2O, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by chromatography provided 1-{4-[4-(2-chloro-benzyl)-piperazin-1-ylmethyl]-benzyl}-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (90 mg, 19%). HPLC-MS 598 [M+1]+, 300. washed with a saturated solution of NaHCO3, H2O dried (Na2SO4) filtered concentrated under reduced pressure Purification by chromatography

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

Procedure: To a mixture of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.39 g, 0.81 mmol) and sodium triacetoxyborohydride (0.322 g, 1.52 mmol) in 1,2-dichloroethane (5 ml) at rt was added 1-(2-chloro-benzyl)-piperazine (0.20 g, 0.95 mmol). The reaction was stirred for 8 h and then washed with a saturated solution of NaHCO3, H2O, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by chromatography provided 1-{4-[4-(2-chloro-benzyl)-piperazin-1-ylmethyl]-benzyl}-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (90 mg, 19%). HPLC-MS 598 [M+1]+, 300. washed with a saturated solution of NaHCO3, H2O dried (Na2SO4) filtered concentrated under reduced pressure Purification by chromatography