Veratraldehyde → 3,4-Dimethoxyphenylethanolamine

To a stirred solution of veratraldehyde(16.6 g) and zinc iodide (50 mg) in anhydrous nitromethane (200 ml) was added trimethylsilyl cyanide (12 g) dropwise under nitrogen. After the resulting mixture was stirred at room temperature for 1 hour, the solvent was removed under reduced pressure. Anhydrous tetrahydrofuran (50 ml) was added to the residue, and the resulting mixture was added under ice cooling to a suspension of lithium aluminum hydride (3.9 g) in anhydrous tetrahydrofuran (200 ml). After that, the resulting mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture, insoluble matter was filtered off, and the solvent was then removed under pressure from the filtrate. Chloroform (300 ml) was added to the residue. The resulting mixture was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The thus-obtained residue was purified by a silica gel column, whereby the title compound (10.8 g, yield: 54.8%) was obtained as colorless crystals.

1. customthe solvent was removed under reduced pressure
2. additionAnhydrous tetrahydrofuran (50 ml) was added to the residue
3. additionthe resulting mixture was added under ice cooling to a suspension of lithium aluminum hydride (3.9 g) in anhydrous tetrahydrofuran (200 ml)
4. stirringAfter that, the resulting mixture was stirred for 1 hour at room temperature
5. additionWater was added to the reaction mixture, insoluble matter
6. filtrationwas filtered off
7. customthe solvent was then removed under pressure from the filtrate
8. additionChloroform (300 ml) was added to the residue
9. washThe resulting mixture was washed with water
10. dry with materialwas then dried over anhydrous sodium sulfate
11. customThe solvent was removed under reduced pressure

ORD record

ord-eb699b1906a642e2adf1075cac67a9f2

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06124347