2,N-二甲基-N-(3,3-二苯基丙基)-1-氨基-2-丙醇的合成

Synthesis of 2,N-dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol

目的研究 2 ,N 二甲基 N (3 ,3 二苯基丙基 ) 1 氨基 2 丙醇 (1 )的合成方法。方法以肉桂酸、氯化亚砜、甲胺等为原料 ,经烃化、氯化、酰化和还原反应得到N 甲基 3 ,3 二苯基丙胺 (5 ) ;以 3 氯异丁烯为原料 ,经加成、水解、环合反应得到环氧异丁烷 (7) ,化合物 5与 7经烃化反应得到目标产物。结果与结论设计的合成路线以肉桂酸计 ,5步反应总收率为 62 7% ,合成路线简便易行 ,适于大规模制备。所合成的目标产物经ESI MS和1H NMR确证。

Aim To investigate a method for the synthesis of 2,N -dimethyl- N -(3,3-diphenylpropyl)-1-amino-2-propanol( 1 ). Methods Alkylation of benzene with cinnamic acid via the Fridel-Crafts reaction gave 3,3- diphenylpropanoic acid,which was subsequently converted to the corresponding acid chloride,then reacted with dried methylamine to obtain N -methyl-3,3-diphenylpropanamide in dichloromethane.This amide was efficiently reduced with the NaBH_4-CH_3COOH/THF system,and the key intermediate N -methyl-3,3-diphenylpropanamine( 5 )was provided in 90% yield.Then 3-chloroisopropene was treated with 80% sulfuric acid followed by hydrolysis to give 1-chloro-2-methyl-2-propanol,which was effected with 7.5 mol/L NaOH using TEBA as a catalyst to provide another key intermediate isobutylene oxide( 7 ).Finally,5 reacted with 7 under refluxing for 12 h without adding a solvent to gain the target molecule in near quantity. Results and conclusion A cost-efficient facile synthetic route that is suitable for large-scale preparation of the target compound has been provided through a five-step procedure starting from cinnamic acid in a total yield of 62.7%,and the structure was verified by ESI-MS and 1H-NMR.