Synthesis
GENERAL PROCEDURE: To a saturated NH4OAc ethanol solution (40 mL) was added activated zinc powder (5 eq.), 2'-methoxyacetophenone (1 eq.), NaBH3CN (3 eq.), and 30% aqueous ammonia solution (10 mL), in that order. The reaction mixture was stirred at 80 °C for 36 hours. After completion of the reaction, it was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved with dichloromethane and adjusted to alkaline with 1 M NaOH aqueous solution (50 mL). The organic phase was separated and the aqueous phase was back-extracted with dichloromethane (2 x 25 mL). The organic phases were combined and acidified with HCl to pH 2.0. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2 x 25 mL). After the aqueous layer was adjusted to pH 10.0 with NaOH, the organic layer was extracted with dichloromethane (3 × 25 mL). The organic layers were combined, dried with anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to obtain the target product 1-(2-methoxyphenyl)ethylamine.
References
[1] Science, 2017, vol. 358, # 6361, p. 326 - 332
[2] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 245 - 252
[3] Farmaco, 1991, vol. 46, # 7-8, p. 861 - 872
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3592 - 3602
[5] Chirality, 2018, vol. 30, # 7, p. 900 - 906
