微波辅助合成1-(3-羟丙基)-4-哌啶酮

Microwave assisted synthesis of 1-(3-hydroxypropyl)-4-piperidone

摘要:

以3-羟基丙胺和丙烯酸甲酯为起始原料，在微波辅助下进行Michael加成、Dieckmann环合和脱羧反应合成了1-(3-羟丙基)-4-哌啶酮。对Michael加成、Dieckmann环合和脱羧反应涉及的工艺参数进行了优化，目标化合物和中间体采用核磁共振波谱进行了表征。结果表明：n(3-羟基丙胺): n(丙烯酸甲酯)=1: 2.4，在功率为120 W的微波辐射和40 ℃下反应30 min，制备得到3-[(2-甲氧羰乙基)(3-羟丙基)氨基]丙酸甲酯，收率为92.6%；在功率为200 W的微波辐射下，Dieckmann环合反应和脱羧反应分别回流反应20 min和25 min，以88.5%的收率得到1-(3-羟丙基)-4-哌啶酮；目标产物总收率为81.9%。

Abstract:

1-(3-Hydroxypropyl)-4-piperidone was prepared from 3-hydroxypropylamine and methyl acrylate through Michael addition, Dieckmann cyclization and decarboxylation reaction under microwave irradiation. The technological parameters involved in Michael addition, Dieckmann cyclization and decarboxylation reaction were optimized. Structures of the target product and the intermediate were confirmed by 1H NMR and 13C NMR. The results show that n(3-hydroxypropylamine):n(methyl acrylate) = 1:2.4 reacted under microwave power 120W and 40℃ for 30min to give methyl 3-[(2-methoxycarbonylethyl)(3-hydroxypropyl)amino]propionate in 92.6%. 1-(3-Hydroxypropyl)-4-piperidone was obtained with the yield of 88.5% under the conditions of microwave power 200W and reflux for 20min and 25min in Dieckmann cyclization and decarboxylation reaction. The total yield of the target product was 81.9%.