Ammonium Acetate → 1-(4-Chloro-2-methylphenoxy)propan-2-amine

Participants

Reaction Steps

120 g of ammonium acetate and 9.8 g of sodium cyanoborohydride were added to a solution containing 31 g of (4-chloro-2-methylphenoxy)acetone dissolved in 700 ml of methanol, and the resultant mixture was stirred for 20 hours at room temperature. After the reaction mixture was concentrated under reduced pressure, 180 ml of concentrated hydrochloric acid and 100 ml of water were added to the residue. The whole mixture was stirred for 1 hour, and then 300 ml of diethyl ether was added thereto. The aqueous layer was alkalified using a 5% aqueous solution of sodium hydroxide, and then extracted with 500 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. A fraction possessing a low boiling point was removed from the obtained oily products to afford 25 g (yield 81 %) of the desired product.

Provenance & Evidence