Asymmetric synthesis, crystal structure, and antidepressant activity of 2-aryl-3-alkyl-5-methyl-2-morpholinol hydrochlorides

作者：Cao, Gao; Hu, Ai Xi^*; Xiao, Xin Rong

来源：Canadian Journal of Chemistry, 2007, 85(1): 29-36.

DOI：10.1139/V06-184

• morpholinol hydrochloride
• hemiacetal
• chiral synthesis
• X-ray diffraction
• absolute configuration
• antidepressant activity

2-Aryl-3-alkyl-5-methyl-2-morpholinols were synthesized from the reactions of chiral 2-aminopropan-1-ol with 2-bromo-1-phenylpropan-1-one, 2-bromo-1-(3-chlorophenyl)propan-1-one, 1-(4-(benzyloxy)phenyl)-2-bromopropan-1-one, 2-bromo-1-(6-methoxy- naphthalen-2-yl)propan-1-one, and 1-(4-(benzyloxy)phenyl)pentan-1-one in N-methyl-2-pyrrolidone (NMP), respectively. The 2-aryl-3-alkyl-5-methyl-2-morpholinols were reacted with hydrogen chloride to give the hydrochloride salts with yields of 56%-77%. The structures of the products were proven by means of their H-1 NMR, IR, and MS spectroscopic data. The stereochemical properties of representative products were established unambiguously by the X-ray single crystal analysis. The antidepressant activities of the title compounds were assayed by the mouse forced swimming test (FST). The FST results confirm the antidepressant properties of our products.

• 出版日期2007-1
• 单位华南理工大学; 湖南大学