Synthesis
The general procedure for the synthesis of 3-(4-methoxyphenyl)propan-1-amine from the compound (CAS: 583825-29-0) was as follows: synthesis of 3-(4-methoxyphenyl)propanamine (13). Amine 13 was prepared by reacting azide 12 (5.2 g, 0.027 mol) with lithium aluminum hydride (LAH, 26 mL of 1 M THF solution) as described in Method A. The crude product 13 was purified by fast column chromatography (silica gel, eluent ratio 2:1:0.05 chloroform/ethanol/concentrated ammonium hydroxide) to give the pure amine 13 (3.2 g, 74% yield) that It was a transparent oily material. Its 1H NMR (300 MHz, CDCl3) data were as follows: δ 1.58 (m, 2H), 2.50 (m, 4H), 3.72 (s, 3H), 6.85 (d, 2H), 7.0 (d, 2H).
References
[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4098 - 4115
[2] Patent: US2003/195160, 2003, A1
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5362 - 5374
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 20, p. 8441 - 8455
