Chloroform → 3-(2,6-Dichlorophenyl)propan-1-amine

Participants

Reaction Steps

To a suspension of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (0.30 g) in chloroform (10 ml) were added oxalyl chloride (0.13 ml) and dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solvent was evaporated under reduced pressure and toluene was added. The mixture was concentrated and chloroform (5 ml) was added. A solution of 3-(2,6-dichlorophenyl)propylamine (0.31 g) obtained in the previous step in chloroform (1 ml) and triethylamine (0.21 ml) were successively added under ice-cooling, and the mixture was stirred under ice-cooling for 10 min. 1N Aqueous hydrochloric acid solution was added to the obtained reaction mixture and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1–1:2) to give N-[3-(2,6-dichlorophenyl)propyl]-3-benzyloxy-4-oxo-4H-pyran-2-carboxamide (0.24 g).

Provenance & Evidence