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 509889

반응식

HRID 509889 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d37267d5e024a74bb317d539b75d7d3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096591B2

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