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

HRID 1199486

反応式

HRID 1199486 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64d4e5b8eb75400cb40fd8fc76cd4e8a
出典データセット
uspto-grants-1990_02
特許番号
US04900835

関連ノート

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