ethyl 4-(2-ethoxy-2-oxoethyl)-1-methyl-4-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】24892

【品名】ethyl 4-(2-ethoxy-2-oxoethyl)-1-methyl-4-piperidinecarboxylate

【CA登记号】

【分子式】C₁₃H₂₃NO₄

【分子量】257.32996

【元素组成】C 60.68% H 9.01% N 5.44% O 24.87%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

The condensation of 1-methyl-4-piperidone (I) with ethyl cyanoacetate (II) in refluxing acetic acid gives ethyl (1-methyl-4-piperidylidene)cyanoacetate (III), which by reaction with KCN in ethanol is converted to ethyl (1-methyl-4-cyano-4-piperidyl)cyanoacetate (IV). The decarboxylative hydrolysis of (IV) with refluxing aqueous HCl affords (1-methyl-4-carboxy-4-piperidyl)acetic acid (V), which is esterified with ethanol - HCl to its diethyl ester (VI). Finally, this compound is treated with ethylamine at 200 C.

参考文献中间体

合成目标

【1】 Bruschweiler, C.; Schereier, E.; Sues, R.; Winkler, H.; Improvements in or relating to Spiropiperidyl-Succinimide Derivatives. CH 411895; CH 449628; GB 1041015 .
【2】 Ghose, K.; RS-86. Drugs Fut 1986, 11, 4, 276.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	10919	1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one	1445-73-4	C₆H₁₁NO	详情	详情
(II)	11877	Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate	105-56-6	C₅H₇NO₂	详情	详情
(III)	24889	ethyl 2-cyano-2-(1-methyl-4-piperidinylidene)acetate		C₁₁H₁₆N₂O₂	详情	详情
(IV)	24890	ethyl 2-cyano-2-(4-cyano-1-methyl-4-piperidinyl)acetate		C₁₂H₁₇N₃O₂	详情	详情
(V)	24891	4-(carboxymethyl)-1-methyl-4-piperidinecarboxylic acid		C₉H₁₅NO₄	详情	详情
(VI)	24892	ethyl 4-(2-ethoxy-2-oxoethyl)-1-methyl-4-piperidinecarboxylate		C₁₃H₂₃NO₄	详情	详情

Extended Information