Dimethylformamide → 8-[4-(4-Pyridinyl)butyl]-8-azaspiro[4.5]decane-7,9-dione

HRID 1639326

반응식

HRID 1639326 반응식
[CH2:1]1[CH2:5][C:4]2([CH2:12][C:10](=[O:11])[NH:9][C:7](=[O:8])[CH2:6]2)[CH2:3][CH2:2]1.[C:13](=O)([O-])[O-].[Cs+].[Cs+].Br.N1C=CC=[CH:22][C:21]=1[CH2:26][CH2:27][CH2:28][CH2:29]Br.[CH3:31][N:32]([CH3:35])C=O>>[N:32]1[CH:35]=[CH:22][C:21]([CH2:26][CH2:27][CH2:28][CH2:29][N:9]2[C:7](=[O:8])[CH2:6][C:4]3([CH2:5][CH2:1][CH2:2][CH2:3]3)[CH2:12][C:10]2=[O:11])=[CH:13][CH:31]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 1368438-Azaspiro(4.5)decane-7,9-dioneHCID 703545584-Pyridinylbutyl bromide hydrobromide

생성물 1

HCID 159257358-[4-(4-Pyridinyl)butyl]-8-azaspiro[4.5]decane-7,9-dione수율 30%

실험 절차

To a stirred solution of 1.8 g. (0.011 mol) of 3,3-tetramethyleneglutarimide in 50 ml. of dimethylformamide is added 3 g. (0.011 mol) of cesium carbonate and 3.2 g. (0.011 mol) of 4-pyridinylbutyl bromide hydrobromide. The reaction mixture is stirred at room temperature for 48 hours, dimethylformamide is evaporated under reduced pressure and the residue is extracted with methylene chloride (3×200 ml.). The methylene chloride extracts are collected, washed with water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The semisolid residue was subjected to HPLC separated using ethyl acetate as eluent. Evaporation of the solvent from the desired fraction (TLC Rf 0.2) affords 1.0 g. (30% yield) of the titled compound which is converted to the hydrochloride salt by dissolving the free base in ethanol and adding ethanol saturated with hydrogen chloride; m.p. 155°-157° C.

후처리

  1. customdimethylformamide is evaporated under reduced pressure
  2. extractionthe residue is extracted with methylene chloride (3×200 ml.)
  3. customThe methylene chloride extracts are collected
  4. washwashed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customseparated
  8. customEvaporation of the solvent from the desired fraction (TLC Rf 0.2)
  9. customaffords 1.0 g

출처 및 근거

ORD 기록
ord-2eeac32f7cfd427b9f3b3d45cb31da9e
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883875

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