Sodium hydride → 2-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone

HRID 710911

반응식

HRID 710911 반응식
[H-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:7]=3[C:6]=2[CH:5]=1.Cl[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21]>CCCCCC.C1COCC1>[Br:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:19][C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])[C:8]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:7]=3[C:6]=2[CH:5]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 1998168-Bromo-2,3,4,5-tetrahydro-2-methyl-1H-pyrido(4,3-b)indoleHCID 2223122-Chloro-1-piperidine-1-yl-ethanone

생성물 1

HCID 447719132-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone수율 51.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

Sodium hydride (0.6 g, 15 mmol) washed with hexane for removal of oil and dried under vacuum. Then sodium hydride was taken in THF. To this solution 8-bromo-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2 g, 7.5 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 (1.8 g, 11.3 mmol) in THF was added drop wise in reaction mixture. Then reaction mixture stirred at rt for 2 h. Reaction was monitored by TLC. After completion of the 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 washed with hexane and diethyl ether for removal of color impurities then recrystallized by using methanol to gives 1.5 g of desired compound then out of that 0.8 g compound was stirred in ethanolic HCl to give HCl salt of 2-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanone.

후처리

  1. customdried under vacuum
  2. customThen reaction mixture
  3. customwise in reaction mixture
  4. customThen reaction mixture
  5. stirringstirred at rt for 2 h
  6. customReaction
  7. customAfter completion of the reaction, reaction mixture
  8. customquench with ice-water
  9. customTHF was evaporated
  10. extractionaqueous layer was extracted with ethyl acetate
  11. dry with materialOrganic layer was dried over anhydrous sodium sulphate
  12. washThe crude compound was washed with hexane and diethyl ether for removal of color impurities
  13. customthen recrystallized

출처 및 근거

ORD 기록
ord-5be4b5254c534bf1af269b39b6f1d721
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181240B2

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