5-(piperidin-1-ylmethyl)furan-2-carbaldehyde

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

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

Procedure: In 100 ml of dry ethanol were dissolved 1.2 g (6.78 mmol) of Compound j and 1.3 g (6.78 mmol) of 5-piperidinomethylfurfural and the solution was stirred at room temperature for 20 hours. The reaction mixture was then cooled with ice and 1.18 g (31.1 mmol) of sodium borohydride was gradually added. The mixture was further stirred under ice-cooling for 1.5 hours. The reaction mixture was then concentrated, and after addition of methylene chloride, the resulting solution was washed with 2 portions of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. Finally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1→chloroform-methanol-triethylamine=100:10:1) to give 1.26 g (52.9%) of Compound 18 as light yellow oil. was gradually added The mixture was further stirred under ice- cooling for 1.5 hours The reaction mixture was then concentrated after addition of methylene chloride the resulting solution was washed with 2 portions of saturated aqueous sodium chloride solution The organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off Finally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1→chloroform-methanol-triethylamine=100:10:1)