Ammonium Acetate → 1-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a mixture of 552.0 mg (1.779 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethanone and molecular sieves in 10 ml methanol were added 1679.0 mg (21.35 mmol) ammonium acetate and 78.0 mg (1.241 mmol) sodium cyanoborohydride and the reaction mixture was stirred 26 h (HPLC control) at 50° C. After cooling to room temperature, the molecular sieves were filtered off and washed with methanol. The solvent of the combined filtrates was evaporated and diethyl ether and water were added to the residue. While stirring the mixture was acidified with 6N aqueous HCl solution to pH2. The aqueous phase was separated and the organic phase was extracted two times with 1N aqueous HCl solution. Ethyl acetate was added to the combined aqueous phases and the mixture was basified with 6N NaOH to pH 10. The organic phase was separated and the aqueous phase was extracted two more times with ethyl acetate. The combined organic phases were dried over MgSO4 and the solvent evaporated at reduced pressure to afford 268.0 mg (0.861 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethylamine.

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