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

Participants

Reaction Conditions

Reaction Steps

{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 342-(2-methylaminoethyl)phenoxy]propan-1-ol. The crude product was used in the next step without further purification.

Provenance & Evidence