Trifluoroacetic acid → 3-[2-(2-Methylaminoethyl)phenoxy]propan-1-ol

Temperature

0 °C

{2-[2-(3-Hydroxypropoxy)phenyl]ethyl}-N-methylcarbamic acid tert-butyl ester (0.587 g, 1.90 mmol) was dissolved in dichloromethane (5 ml). The solution was cooled to 0° C. Trifluoroacetic acid (5 ml) was added. The reaction mixture was stirred for 30 min at 0° C. Dichloromethane (50 ml) was added. A saturated aqueous solution of sodium hydrogen carbonate (50 ml) was added dropwise. Solid sodium hydrogen carbonate was added, until pH 7 was obtained. The phases were separated. The aqueous solution was extracted with dichloromethane (3×70 ml). The aqueous phase was made basic to pH 14 with a 20% aqueous sodium hydroxide solution. It was extracted with tert-butyl methyl ether (3×100 ml). The tert-butyl methyl ether extracts were combined and dried over magnesium sulfate. The solvent was removed in vacuo to give 227 mg of crude 3-[2-(2-methylaminoethyl)phenoxy]propan-1-ol. The crude product was used in the next step without further purification.

1. customwas obtained
2. customThe phases were separated
3. extractionThe aqueous solution was extracted with dichloromethane (3×70 ml)
4. extractionIt was extracted with tert-butyl methyl ether (3×100 ml)
5. dry with materialdried over magnesium sulfate
6. customThe solvent was removed in vacuo

ORD record

ord-0c7166141b6549bb8245627d83cd81a6

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127354