Dimethylamine → HCID 67404297, compound

Participants

Reaction Steps

4-(2,2,2-Trifluoro-1-hydroxyethyl)benzaldehyde (295 mg, 1.4 mmol) obtained in Step 1 of Reference Example 8-70 was dissolved in acetonitrile (15 mL). To this, dimethylamine (a 1.0 mol/L solution in tetrahydrofuran, 7.2 mL, 14 mmol) and acetic acid (0.83 mL) were added and the mixture was stirred at room temperature for 30 minutes. To this, sodium triacetoxyborohydride (918 mg, 4.3 mmol) was added and the mixture was stirred at room temperature for 4 hours. Then, an aqueous sodium bicarbonate solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was subjected to slurry purification using a mixed solvent of diisopropyl ether and hexane. Further, purification by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/1) was performed to give 1-{4-[(dimethylamino)methyl]phenyl}-2,2,2-trifluoroethanol (Compound ER) (284 mg, yield: 85%).

Provenance & Evidence