引用本文:
王平, 尹传奇, 申永存, 滕汉兵. 3-奎宁酮盐酸盐的合成[J]. 应用化学,
2008, 25(5): 626-628.
Citation: WANG Ping, YIN Chuan-Qi, SHEN Yong-Cun, TENG Han-Bing. Synthesis of 3-Quinuclidinone Hydrochloride[J]. Chinese Journal of Applied Chemistry, 2008, 25(5): 626-628.
Citation: WANG Ping, YIN Chuan-Qi, SHEN Yong-Cun, TENG Han-Bing. Synthesis of 3-Quinuclidinone Hydrochloride[J]. Chinese Journal of Applied Chemistry, 2008, 25(5): 626-628.
3-奎宁酮盐酸盐的合成
摘要:
以氯化亚砜作氯化剂,4-哌啶甲酸(Ⅰ)在无水乙醇中以95%的产率酯化生成4-哌啶甲酸乙酯盐酸盐(Ⅱ);化合物Ⅱ在丙酮中与氯乙酸乙酯在碳酸钾的催化下发生N-烷基化反应生成N-乙氧羰酰乙基-4-哌啶甲酸乙酯(Ⅲ),收率85%;化合物Ⅲ在强碱性条件下发生分子内酯缩合(Dieckmann condensation)生成2-乙氧羰基-3-奎宁酮(Ⅳ),化合物Ⅳ在强酸性条件下脱酸得到3-奎宁酮盐酸盐(V),2步收率达73%;以化合物Ⅰ为原料合成化合物V的产率为58%;产物经IR、NMR、MS测试技术证实。
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关键词:
- 奎宁酮盐酸盐
- / Dieckmann缩合
- / 合成
English
Synthesis of 3-Quinuclidinone Hydrochloride
Abstract:
With thionyl chloride as a chlorination agent,ethyl 4-piperidinecarboxylic acid hydrochloride (Ⅱ) was synthesized by the esterification of 4-piperidinecarboxylic acid (Ⅰ) with ethanol in a yield of 95%,which was reacted with ethyl chloroacetate in acetone to give 1-carbethoxymethyl-4-carbethoxypiperidine (Ⅲ) in a yield of 85%;2-carbethoxy-3-quinuclidinone (Ⅳ) was prepared by the Dieckmann condensation of compound (Ⅲ) under strong basic condition,which was decarboxylated in a yield of 73% under strong-acidic condition,and the total yield was 58%.The product structures was confirmed by IR,1H NMR and MS.
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Key words:
- quinuclidinone hydrochloride
- / Dieckmann condensation
- / synthesis
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