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

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).

1. customThe reaction solvent was evaporated under reduced pressure and toluene
2. additionwas added
3. concentrationThe mixture was concentrated
4. additionchloroform (5 ml) was added

ORD record

ord-362c73f8bd8e48bf9db5a0c4ad1c4ab0

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07211572B2