机构地区: 湖南大学化学化工学院
出 处: 《湖南大学学报(自然科学版)》 2005年第4期72-76,共5页
摘 要: α-溴-4-甲氧基苯乙酮、α-溴-2-氟苯丙酮、α-溴-4-苄氧基苯丙酮、6-甲氧基-2-(溴乙酰基)萘、6-甲氧基-2-(2-溴丙酰基)萘分别与二乙醇胺、2-氨基-1-丙醇、N-甲基乙醇胺、2-甲基-2-氨基-1-丙醇和甲酸发生非经典Leuckart-Wallach反应,合成相应的2-芳基吗啉,后者经盐酸酸化成盐,得到4-羟乙基-2-(4-甲氧基苯基)吗啉、盐酸3-甲基-4-羟乙基-2-(2-氟苯基)吗啉、盐酸3-甲基-4-羟乙基-2-(4-苄氧基苯基)吗啉、盐酸4-羟乙基-2-(6-甲氧基-2-萘基)吗啉、盐酸3-甲基-4-羟乙基-2-(6-甲氧基-2-萘基)吗啉、盐酸3,4-二甲基-2-(6-甲氧基-2-萘基)吗啉、盐酸3,5-二甲基-2-(6-甲氧基-2-萘基)吗啉和盐酸3,5,5-三甲基-2-(6-甲氧基-2-萘基)吗啉.产率为15.6%~58.9%.其结构经1H NMR,1H-1H COSY,IR,MS确证. 4- ( 2-Hydroxyethyl )-2- ( 4-methoxyphenyl ) morpholine, 2- ( 2-fluorophenyl )-4- ( 2-Hydroxyethyl ) -3-methyl-morpholine, 2-( 4-benzyloxyphenyl )-3-methyl-4-( 2-hydroxyethyl ) morpholine, 4-( 2-hydroxyethyl )- 2-( 6-methoxy-2-naphthyl )-morpholine, 4-( 2-hydroxyethyl)-2-( 6-methoxy-2-naphthyl )-3-methylmorpholine, 3,4-dimethyl-2-(6-methoxy-2- naphthyl)-morpholine, 3,5-dimethyl-2- ( 6-methoxy-2- naphthyl) morpholine and 3,5,5-trirnethyl-2- (6-methoxy-2-naphthyl)morpholine were synthesized via the reactions of α-bromo-4-methoxyacetophenone, α-bromo-2-fluoropropiophenone, α-bromo-4-benzyloxypropiophenone, 6- methoxy- 2- (2-bromoacetyl) naphthalene, 6-methoxy-2- (2-bromopropionyl) naphthalene with diethanolamine, 2-amino-1- propanol, N-methyl-ethanolamine, 2-methyl-2- amino-1-propanol , respectively, in a non-protonic polar solvent at 50℃ for 1 h with stirring. Then the mixture was reduced by formic acid at 180℃ reflux for 10 h. The 2-arylmorpholines were reacted with hydrochloride to give the hydrochloride salt with yield of 15.6%-58.9%. The structures of the hydrochloride salts of 2-aryl-morpholines were characterized by ^1H NMR, ^1H-^1H COSY, IR and MS spectra.