3'-Bromoacetophenone → 1-(3-Bromophenyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4.97 g (0.0249 mol) 1-(3-bromo-phenyl)-ethanone and molecular sieves in 50 ml methanol, 23 g (0.298 mol) ammonium acetate and 1.75 g (0.0265 mol) sodium cyanoborohydride were added and the reaction mixture was stirred 2 d (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 ethyl acetate and water were added to the residue. While stirring the mixture was acidified with 6N aqueous HCl solution. 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. The organic phase was separated and the aqueous phase was extracted two more times with ethyl acetate. The organic combined organic phases were dried over MgSO4 and the solvent evaporated at reduced pressure to afford 2.96 g (0.0148 mol) 1-(3-bromo-phenyl)-ethylamine.

Provenance & Evidence