1-Butyl-4,4-dimethyl-2,6-dioxo-3,5-piperidinedicarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】11880

【品名】1-Butyl-4,4-dimethyl-2,6-dioxo-3,5-piperidinedicarbonitrile

【CA登记号】

【分子式】C₁₃H₁₇N₃O₂

【分子量】247.297

【元素组成】C 63.14% H 6.93% N 16.99% O 12.94%

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：(IV)

For the synthesis of umespirone the following synthesis pathway was chosen: Acetone is condensed with ethyl cyanoethanoate (I) to yield ethylisopropylidenecyanoacetate (II). This product is reacted with N-butylcyanoacetamide (III) in sodium methoxide solution to give N-butyl-2,4-dicyano-3,3-dimethylglutarimide (IV). The glutarimide (IV) is cyclized with phosphoric acid to yield 3-butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone (V). The quaternary salt (VIII) (R = CH3), prepared from 1-(2-methoxyphenyl)piperazine (VI) and 1,4-dibromobutane (VII), undergoes reaction with (V) in the presence of potassium carbonate to afford the free base KC-9172 (IX) (R = CH3).

参考文献中间体

合成目标

【1】 Schon, U.; Kehrbach, W.; Benson, W.; Fuchs, A.; Ruhland, M. (Kali-Chemie AG); Novel tetraoxo cpds. AU 8661619; DE 3529872; EP 0212551; ES 8801271; ES 8801272; US 4771044 .
【2】 Krahling, H.; Krijzer, F.; Umespirone. Drugs Fut 1991, 16, 5, 437.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	23199	2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether	67-64-1	C₃H₆O	详情	详情
(I)	11877	Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate	105-56-6	C₅H₇NO₂	详情	详情
(II)	11878	ethyl 2-cyano-3-methyl-2-butenoate; 2-Butenoic acid, 2-cyano-3-methyl-, ethyl ester	759-58-0	C₈H₁₁NO₂	详情	详情
(III)	11879	N-Butyl-2-cyanoacetamide		C₇H₁₂N₂O	详情	详情
(IV)	11880	1-Butyl-4,4-dimethyl-2,6-dioxo-3,5-piperidinedicarbonitrile		C₁₃H₁₇N₃O₂	详情	详情
(V)	11881	3-Butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetrone		C₁₃H₁₈N₂O₄	详情	详情
(VI)	11882	1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine	35386-24-4	C₁₁H₁₆N₂O	详情	详情
(VII)	11883	1,4-Dibromobutane; 1,4-Butylene bromide	110-52-1	C₄H₈Br₂	详情	详情
(VIII)	11884	8-(2-Methoxyphenyl)-8-aza-5-azoniaspiro[4.5]decane bromide		C₁₅H₂₃BrN₂O	详情	详情

Extended Information