Hydrochloric Acid → 2-((2-Furanylmethyl)sulfinyl)-N-(3-(3-(1-piperidinylmethyl)phenoxy)propyl)acetamide

Participants

Reaction Steps

N-[3-(3-formylphenoxy)propyl]-2-(furfurylsulfinyl)acetamide (13.85 g) was dissolved in 150 ml of ethanol, and while 5.06 g of piperidine was added dropwise, the mixture was stirred at room temperature for 15 hours. The reaction solution was cooled with ice, and 1.5 g of sodium borohydride was added. The mixture was stirred for 5 hours. 1N-HCl was added to the reaction solution to make it acidic, and the solvent was evaporated. The residue was poured into water and extracted with ethyl acetate. The aqueous layer was made basic by adding anhydrous sodium carbonate, and extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5) to give 8.80 g (yield 53%) of N-{3-[3-(piperidinomethyl)phenoxy] propyl]-2-(furfurylsulfinyl) acetamide.

Provenance & Evidence