聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → N-(1-Azabicyclo[2.2.2]oct-3-yl)-2,4-dimethoxybenzamide hydrochloride

HRID 3761

反应方程式

HRID 3761 反应方程式
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[CH3:12][O:13][C:14]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:15]=1[C:16]([Cl:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+].O>C(Cl)(Cl)Cl>[ClH:18].[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[CH:4]([NH:3][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:14]=1[O:13][CH3:12])[CH2:5]2

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 10340Carbonic acid sodium salt (1:2)HCID 1978533-氨基奎宁环盐酸盐HCID 27347192,4-二甲氧基苯甲酰氯

产物 1

HCID 13272330N-(1-Azabicyclo[2.2.2]oct-3-yl)-2,4-dimethoxybenzamide hydrochloride收率 23.7%

试剂、催化剂与溶剂 1

HCID 6212三氯甲烷溶剂

实验过程

A mixture of 3-aminoquinuclidine dihydrochloride, 6.95 g, (0.349), 2,4-dimethoxybenzoyl chloride, 700 g, (0.0349 mole), anhydrous sodium carbonate, 36.99 g, (0.349 mole), 175 ml water, and 175 ml chloroform was stirred rapidly to achieve good mixing of the 2 layers for 20 hrs. The chloroform layer was then separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated to an impure oil. The oil was triturated twice with 20 ml portions of petroleum ether to remove some impurities. The oil was then dissolved in diethyl ether and filtered to remove a small amount of insoluble material. The filtrate was treated with ethereal hydrogen chloride and the resulting salt collected to yield 2.70 g (23.7% yield) white solid. The salt was recrystallized from ethanol-isopropyl ether. Further recrystallization from methanol-ethyl ether yielded a white solid, m.p. 211°-212° C. The NMR analysis was satisfactory.

后处理

  1. additionto achieve good mixing of the 2 layers for 20 hrs
  2. customThe chloroform layer was then separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to an impure oil
  6. customThe oil was triturated twice with 20 ml portions of petroleum ether
  7. customto remove some impurities
  8. dissolutionThe oil was then dissolved in diethyl ether
  9. filtrationfiltered
  10. customto remove a small amount of insoluble material
  11. additionThe filtrate was treated with ethereal hydrogen chloride
  12. customthe resulting salt collected

来源与证据

ORD记录
ord-217b10af343044bfa5761f4da10eaeb8
来源数据集
uspto-grants-1988_02
专利号
US04722834

关联笔记

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