Water → N-(1-Azabicyclo[2.2.2]oct-3-yl)-2,4-dimethoxybenzamide hydrochloride

HRID 3761

反応式

HRID 3761 の反応式
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

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 27347192,4-Dimethoxybenzoyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-217b10af343044bfa5761f4da10eaeb8
出典データセット
uspto-grants-1988_02
特許番号
US04722834

関連ノート

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