三乙胺 → N-[(3-chlorophenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine

HRID 349216

反应方程式

HRID 349216 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.CCN(CC)CC.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.[OH-].[Na+].O>[Cl:19][C:20]1[CH:21]=[C:22]([CH2:23][NH:3][CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[CH:25]=[CH:26][CH:27]=1

参与物

8

反应物 4

HCID 8471三乙胺HCID 114773-氯苯甲醛HCID 1978533-氨基奎宁环盐酸盐HCID 5049666三乙酰氧基硼氢化钠

产物 1

HCID 17158964N-[(3-chlorophenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine收率 30%

试剂、催化剂与溶剂 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂HCID 14798二甲基对苯二胺二盐酸溶剂

实验过程

A mixture of of 3-aminoquinuclidine dihydrochloride (2.0 g, 10.0 mmol), NEt3 (1.3 mL) and 3-chlorobenzaldehyde (1.5 g, 11.0 mmol) in THF (50 mL) was stirred at room temperature. To this was added Na(OAc)3BH 13.2 g, 15 mmol) and the reaction was stirred overnight. The reaction mixture was diluted with 3N NaOH and water and extracted with EtOAc. The organic extracts were combined, washed with water and then brine and dried over K2CO3. The solution was filtered and the solvent was evaporated in vacuo to give an oil which was chromatographed on silica (94/6 CHCl3/0.5 M NH3 in MeOH). The appropriate fractions were combined and the solvent was evaporated in vacuo to give N-[(3-chlorophenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine (0.75 g, 30%) as an intermediate, a light yellow semi-solid. MH+=251,253. The 1H NMR was consistent with the assigned structure.

后处理

  1. stirringwas stirred overnight
  2. extractionextracted with EtOAc
  3. washwashed with water
  4. dry with materialbrine and dried over K2CO3
  5. filtrationThe solution was filtered
  6. customthe solvent was evaporated in vacuo
  7. customto give an oil which
  8. customwas chromatographed on silica (94/6 CHCl3/0.5 M NH3 in MeOH)
  9. customthe solvent was evaporated in vacuo

来源与证据

ORD记录
ord-91f1822674c442d28b532453a12610e5
来源数据集
uspto-grants-2007_02
专利号
US07179818B2

关联笔记

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