Calcium Carbonate → HCID 22929977, compound

After dissolving methyl 2-(dimethylamino)-4-(hydroxymethyl)benzoate (1.023 g, 4.9 mmol) in a methylene chloride (15 ml) and methanol (6 ml) mixed solvent, calcium carbonate (2 g) was added, the mixture was stirred, and then benzyltrimethylammonium tribromide (2.100 g, 5.4 mmol) was gradually added and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was filtered and the solvent was distilled off under reduced pressure. Water was added to the residue, extraction was performed with ethyl acetate and the ethyl acetate layer was washed with water and brine. The aqueous layer was then extracted with a methylene chloride and methanol mixed solvent, combined with the ethyl acetate layer, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.179 g) as a white solid. (84% yield)

1. additionwas added
2. stirringthe mixture was stirred at room temperature for 50 minutes
3. filtrationThe reaction mixture was filtered
4. distillationthe solvent was distilled off under reduced pressure
5. additionWater was added to the residue, extraction
6. washthe ethyl acetate layer was washed with water and brine
7. extractionThe aqueous layer was then extracted with a methylene chloride and methanol mixed solvent
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationThe solvent was distilled off under reduced pressure
10. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

ORD record

ord-d5ae6de2911a4fbdb8535486d08227a8

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07244730B2