盐酸2-芳基吗啉的合成与表征

Synthesis and Characterization of 2-Arylmorpholine Hydrochloride

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.