2-Chloro-1-piperidine-1-yl-ethanone → 2-(1,2,3,4-Tetrahydro-8-iodo-2-methylpyrido[4,3-b]indol-5-yl)-1-(piperidin-1-yl)ethanone

HRID 2196034

反応式

HRID 2196034 の反応式
[I:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.Cl[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19]>C1COCC1>[I:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:17][C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 594549742,3,4,5-Tetrahydro-8-iodo-2-methyl-1h-pyrido[4,3-b]indole

生成物 1

HCID 578763662-(1,2,3,4-Tetrahydro-8-iodo-2-methylpyrido[4,3-b]indol-5-yl)-1-(piperidin-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Sodium hydride was washed with hexane for removal of oil and dried under vacuum. Then sodium hydride was taken in THF. To this solution 8-iodo-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.32 mmol) in THF was added drop wise at 0° C. Then reaction mixture stirred for 0.5 h. The solution of 2-chloro-1-(piperidin-1-yl)ethanone in THF was added drop wise in reaction mixture. Then reaction mixture stirred at rt for 2 h. Reaction monitored by TLC, after completion of reaction, reaction mixture quench with ice-water. THF was evaporated and aqueous layer was extracted with ethyl acetate. Organic layer was dried over anhydrous sodium sulphate. The crude compound was purified by column chromatography to gives 25 mg of desired compound. Out of that 5 mg was stirred with ethanolic HCl to give HCl salt of 2-(8-iodo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone.

後処理

  1. washSodium hydride was washed with hexane for removal of oil
  2. customdried under vacuum
  3. customThen reaction mixture
  4. customwise in reaction mixture
  5. customThen reaction mixture
  6. stirringstirred at rt for 2 h
  7. customReaction
  8. customafter completion of reaction, reaction mixture
  9. customquench with ice-water
  10. customTHF was evaporated
  11. extractionaqueous layer was extracted with ethyl acetate
  12. dry with materialOrganic layer was dried over anhydrous sodium sulphate
  13. customThe crude compound was purified by column chromatography

出典と根拠

ORDレコード
ord-44987ef253fd4cf784e352c92fd72f62
出典データセット
uspto-grants-2012_12
特許番号
US08338408B2

関連ノート

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