4-(2-methoxyethoxy)benzaldehyde

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

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

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

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

Procedure: The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (1.3 gmg, 9.99 mmol), 4-(2-methoxyethoxy)benzaldehyde (1.5 g, 8.33 mmol), TMSCN (1.64 mL, 16.66 mmol) 10% Pd—C (200 mg), TEA (2.5 mL, 18.40 mmol), di-(imidazol-1-yl)methanone (1.192 g, 7.36 mmol), as described in method 2. The product was purified by means of preparative HPLC. The product was purified by means of preparative HPLC

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

Procedure: The compound was synthesized as trifluoroacetate salt starting from 5-aminobenzimidazole (1.3 gmg, 9.99 mmol), 4-(2-methoxyethoxy)benzaldehyde (1.5 g, 8.33 mmol), TMSCN (1.64 mL, 16.66 mmol) 10% Pd—C (200 mg), TEA (2.5 mL, 18.40 mmol), di-(imidazol-1-yl)methanone (1.192 g, 7.36 mmol), as described in method 2. The product was purified by means of preparative HPLC. The product was purified by means of preparative HPLC

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

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 146.5 g (1.2 mol) of 4-hydroxybenzaldehyde are dissolved in DMF, and 20 g (0.12 mol) of potassium iodide, 134.6 g (1.2 mol) of potassium tert-butoxide and 170.2 g (1.8 mol) of 2-chloroethyl methyl ether are added. The reaction mixture is stirred at 80° C. for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure. The residue is taken up in 1 l of ethyl acetate and extracted with 0.5 l of 1N aqueous sodium hydroxide solution. The ethyl acetate phase is dried using magnesium sulphate and concentrated under reduced pressure. The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar). This gives 184.2 g (85% of theory) of product. For work-up, the reaction mixture is concentrated under reduced pressure extracted with 0.5 l of 1N aqueous sodium hydroxide solution The ethyl acetate phase is dried concentrated under reduced pressure The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 146.5 g (1.2 mol) of 4-hydroxybenzaldehyde are dissolved in DMF, and 20 g (0.12 mol) of potassium iodide, 134.6 g (1.2 mol) of potassium tert-butoxide and 170.2 g (1.8 mol) of 2-chloroethyl methyl ether are added. The reaction mixture is stirred at 80° C. for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure. The residue is taken up in 1 l of ethyl acetate and extracted with 0.5 l of 1N aqueous sodium hydroxide solution. The ethyl acetate phase is dried using magnesium sulphate and concentrated under reduced pressure. The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar). This gives 184.2 g (85% of theory) of product. For work-up, the reaction mixture is concentrated under reduced pressure extracted with 0.5 l of 1N aqueous sodium hydroxide solution The ethyl acetate phase is dried concentrated under reduced pressure The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 146.5 g (1.2 mol) of 4-hydroxybenzaldehyde are dissolved in DMF, and 20 g (0.12 mol) of potassium iodide, 134.6 g (1.2 mol) of potassium tert-butoxide and 170.2 g (1.8 mol) of 2-chloroethyl methyl ether are added. The reaction mixture is stirred at 80° C. for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure. The residue is taken up in 1 l of ethyl acetate and extracted with 0.5 l of 1N aqueous sodium hydroxide solution. The ethyl acetate phase is dried using magnesium sulphate and concentrated under reduced pressure. The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar). This gives 184.2 g (85% of theory) of product. For work-up, the reaction mixture is concentrated under reduced pressure extracted with 0.5 l of 1N aqueous sodium hydroxide solution The ethyl acetate phase is dried concentrated under reduced pressure The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar)

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

Procedure: A solution of 2.2 grams (0.0050 mole) of 4-{bis[4-(trifluoromethoxy)phenyl]methyl}piperidin-4-ol, 1.1 grams (0.0061 mole) of 4-(2-methoxyethoxy)benzaldehyde and 1.35 grams (0.0064 mole) of sodium triacetoxyborohydride in 25 mL of methylene chloride was stirred at ambient temperature for 18 hours. The reaction mixture was then diluted with 200 mL of water and stirred at ambient temperature for 5 hours. The phases were separated. The organic phase was washed three times; first, with 100 mL of an aqueous mixture of 10% sodium hydroxide, second, with 100 mL of an aqueous mixture of 10% lithium chloride, and, third, with 100 mL of brine. The resultant organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using methylene chloride:1%-5% methanol as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 2.2 grams of the subject compound. The NMR spectrum was consistent with the proposed structure. The phases were separated The organic phase was washed three times The resultant organic layer was dried over magnesium sulfate filtered concentrated under reduced pressure to a residue The residue was purified with column chromatography on silica gel concentrated under reduced pressure