温和条件下2-[苯基(苯胺基)甲基]环己酮的一锅法催化合成

分别采用SnCl4.5H2O、对甲苯磺酸、NaHSO4.H2O和KHSO4催化苯胺、苯甲醛和环己酮的Mannich缩合反应一锅法合成了2-苯基(苯胺基)甲基]环己酮(PPMC)。系统考察了原料配比n(环己酮)∶n(苯胺)及n(苯甲醛)∶n(苯胺)、催化剂用量、反应温度和反应时间对PPMC收率的影响,并就四种催化剂催化性能进行了比较。实验结果表明,适宜反应条件为n(苯甲醛)∶n(苯胺)∶n(环己酮)=1∶1∶1.2,催化剂用量为反应物总质量的3.36%～13.45%,反应温度15～25℃,反应时间1～4h,PPMC收率为77.4%～84.2%。其中SnCl4.5H2O和对甲苯磺酸具有较理想的催化活性,催化剂用量少,反应时间短,收率高。该合成工艺路线简捷,催化剂价廉易得,使用方便,反应条件温和,收率可观。

One-pot Catalytic Synthesis of 2-[Phenyl(phenylamino) methyl] cyclohexanone Under Mild Conditions

An efficient and direct procedure was developed for the preparation of 2-phenyl(phenylamino)methyl]cyclohexanone(PPMC) by a three-component one-pot Mannich reaction of benzaldehyde,aniline and cyclohexanone in the presence of SnCl4·5H2O,p-toluene sulphonic acid,NaHSO4·H2O or KHSO4 as catalyst,respectively.The Mannich reaction was carried out with n(benzaldehyde)∶n(aniline)∶n(cyclohexanone)=1∶1∶1.2 and mass fraction of catalyst in all of reactants 3.36%~13.45% at 15~25℃ for 1~4 h.The yield of PPMC was 77.4%~84.2%.SnCl4·5H2O and p-toluene sulphonic acid showed good catalytic activity for the reaction.The mild reaction conditions offer several advantages such as inexpensive,better yield and easy work-up.The catalysts make the procedure an attractive alternative to the existing methods for the synthesis of the product.