Sulfuric Acid → (1-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidin-4-yl)methanamine

HRID 46003ノート

反応式

HRID 46003 の反応式
OS(O)(=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([N:27]2[CH2:32][CH2:31][N:30]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)([C:25]#[N:26])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([CH2:25][NH2:26])([N:27]2[CH2:28][CH2:29][N:30]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[CH2:31][CH2:32]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 686295031-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidine-4-carbonitrile

生成物 1

HCID 57989584(1-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidin-4-yl)methanamine収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

H2SO4 (1.5 equiv.) was added to a suspension of LAH (3 equiv.) in THF (32 ml) at 0° C. and the mixture was stirred at room temperature for 0.5 h. A solution of 1-benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidine-4-carbonitrile (5.54 mmol, 1 equiv.) in THF was added under cooled conditions and the resulting reaction mixture was heated to 50° C. for 16 h. The reaction was quenched with THF/H2O solution, filtered and the solid residue washed with excess ethyl acetate. The organic layer was given a brine wash, dried over sodium sulfate and the solvent was removed under reduced pressure. The resulting crude product was used for the next step without further purification. Yield: 85%.

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas heated to 50° C. for 16 h
  3. customThe reaction was quenched with THF/H2O solution
  4. filtrationfiltered
  5. washthe solid residue washed with excess ethyl acetate
  6. washwash
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe resulting crude product was used for the next step without further purification

出典と根拠

ORDレコード
ord-50e858841fe74112aab7551f9fc91960
出典データセット
uspto-grants-2013_09
特許番号
US08541573B2

反応ノート

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