4-(3-氯苯乙基)呱啶的简便合成

Concise Synthesis of 4-(3-Chlorophenethyl)piperidine

以廉价易得的N-Boc呱啶-4-甲醇(1)和间氯苄氯(3)为原料,经Swern氧化、Wittig反应、钯碳催化加氢和脱保护基反应合成目标化合物4-(3-氯苯乙基)呱啶盐酸盐(7)。路线总收率达到56%,化学纯度96.6%。加氢不脱氯反应的最佳反应条件为:以含量为10%干钯碳催化加氢,二氧六环为溶剂,反应时间3h。化合物7的结构及纯度经^(1)H NMR,^(13)C NMR和MS(EI)确证。该合成方法具有反应条件温和、操作简单、收率高等优点。

The target compound 4-(3-chlorophenylethyl)piperidine hydrochloride(7)was synthesized via Swern oxidation,Wittig reaction,Pd-catalytic hydrogenation and deprotection reaction from tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylatein(1)as raw material.Optimized reaction conditions:dry palladium carbon catalyzed hydrogenation in dioxane for 3 h at rt,the total yield of 7 was 56%and the purity was 96.6%.The structure was confirmed by ^(1)H NMR,^(13)C NMR and MS(EI).The synthetic method with high yield displayed the advantages of mild reaction condition and simple operation.