Dimethylamine → 3-Bromo-4-methoxy-N,N-dimethylbenzenemethanamine

To a solution of 10.0 g of 3-bromo-4-methoxy benzaldehyde in MeOH (155 ml) was added an aqueous solution of 50% dimethylamine (2.52 ml) and the reaction mixture was stirred at room temperature for 30 minutes. Thereafter, to the solution was added 4.38 g of sodium cyanoborohydride, the reaction mixture was stirred for 15 hours under the same temperature condition, and the reaction solution was concentrated under reduced pressure. Water was added to the residue and extracted with CHCl3; the organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/hexane=1/1, then, MeOH/CHCl3=1/9; v/v) to obtain 2.20 g of the title compound (colorless oil).

1. stirringthe reaction mixture was stirred for 15 hours under the same temperature condition
2. concentrationthe reaction solution was concentrated under reduced pressure
3. additionWater was added to the residue
4. extractionextracted with CHCl3
5. washthe organic layer was washed with saturated brine
6. dry with materialdried over MgSO4
7. customthe drying agent was separated by filtration
8. customthe solvent was evaporated under reduced pressure
9. customThe obtained residue was purified by column chromatography (silicagel 60

ORD record

ord-a579b02b081a4c4c8d45a1a4939c9dbb

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030499B2