Tetrahydrofuran → 1-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

HRID 74561

反応式

HRID 74561 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH2:22]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C[O:39]CC1>>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:11]2[C:2]([Cl:1])=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][C:7]([O:12][CH3:13])=[CH:6][CH:5]=3)([OH:39])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 836472-Chloro-6-methoxyquinolineHCID 2724682Lithium diisopropylamideHCID 51700761-Benzyl-2-piperidone

生成物 1

HCID 581811261-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

反応条件

温度
-78 °C

実験手順

Under an argon atmosphere 5.0 g (25 mmol) 2-chloro-6-methoxyquinoline in a small amount of THF were added dropwise at −78° C. to 14 mL (28 mmol) of a 2 M lithium diisopropylamide solution (in THF) in 50 mL THF. Then the mixture was stirred for 1.5 h at −78° C. and 4.5 mL (25 mmol) N-benzylpiperidone was added dropwise. The mixture was stirred for a further 15 min with cooling before slowly being heated to RT. The reaction mixture was stirred overnight, evaporated down and purified by flash chromatography on aluminium oxide. The product-containing fractions were combined and evaporated down.

後処理

  1. stirringThe mixture was stirred for a further 15 min
  2. temperaturewith cooling
  3. temperaturebefore slowly being heated to RT
  4. stirringThe reaction mixture was stirred overnight
  5. customevaporated down
  6. custompurified by flash chromatography on aluminium oxide
  7. customevaporated down

出典と根拠

ORDレコード
ord-9443c894840b43aa8c4008ecd5502c39
出典データセット
uspto-grants-2014_09
特許番号
US08829006B2

関連ノート

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