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【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).

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