Hydrochloric Acid → [(2,4-Dimethoxyphenyl)methyl](methyl)amine

2,4-Dimethoxybenzaldehyde (5.0 g) was dissolved in methanol (60 mL), and a 40% methanol solution (9.3 mL) of methylamine was added at room temperature. The mixture was stirred at room temperature for 1 hr, and sodium borohydride (1.37 g) was added by small portions under ice-cooling. The mixture was stirred at room temperature for 3 hr, treated with 1 mol/L hydrochloric acid under ice-cooling, and methanol was evaporated under reduced pressure. The residue was diluted with ethyl acetate, basified with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1→2:1) to give the title compound as a colorless oil (yield 4.41 g, 81%).

1. temperaturecooling
2. stirringThe mixture was stirred at room temperature for 3 hr
3. temperaturecooling
4. custommethanol was evaporated under reduced pressure
5. additionThe residue was diluted with ethyl acetate
6. extractionextracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1→2:1)

ORD record

ord-ebcde0bc413b4de382768e90dc2c129d

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933105B2