Halite (NaCl) → N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochloride

HRID 5501

反应方程式

HRID 5501 反应方程式
[OH-].[K+].Cl.Cl.[NH2:5][CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1.[Cl-].[Na+].[Cl:16][CH2:17][C:18](Cl)=[O:19]>O.C(Cl)Cl>[ClH:16].[N:8]12[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9]1)[CH:6]([NH:5][C:18](=[O:19])[CH2:17][Cl:16])[CH2:7]2

参与物

7

反应物 4

HCID 5234Halite (NaCl)HCID 6577氯乙酰氯HCID 14797氢氧化钾HCID 1978533-氨基奎宁环盐酸盐

产物 1

HCID 131716900N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochloride收率 144%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂2 次

实验过程

Potassium hydroxide (10 g) was added to a solution of 3-aminoquinuclidine dihydrochloride (10.45 g, 0.052 mole) in water (80 ml) saturated with sodium chloride. After stirring for 30 minutes, methylene chloride (75 ml) was added and the layers separated. The aqueous layer was washed with methylene chloride (2×75 ml), and the extracts combined with the methylene chloride layer above; dried over sodium sulfate, filtered, and the volume reduced to 100 ml. A solution of chloroacetyl chloride (3.11 g, 0.0273 mole) in methylene chloride (25 ml) was added dropwise and the mixture stirred overnight. The solvent was removed on a rotary evaporator. The residue was recrystallized from methanol-ethyl acetate to give a white solid (4.7 g), m.p. ca. 189°-195° C. The structure was confirmed by NMR.

后处理

  1. customthe layers separated
  2. washThe aqueous layer was washed with methylene chloride (2×75 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. stirringthe mixture stirred overnight
  6. customThe solvent was removed on a rotary evaporator
  7. customThe residue was recrystallized from methanol-ethyl acetate

来源与证据

ORD记录
ord-0036974a8e5f42138d995cc37559e5bb
来源数据集
uspto-grants-1993_09
专利号
US05244899

关联笔记

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