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 509891

Reaktionsgleichung

Reaktionsgleichung von HRID 509891
[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

Komponenten

6

Edukt 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

Produkt 1

HCID 447719132-(8-bromo-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(piperidin-1-yl)ethanoneAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-49177dfb037c485d9b782290c2518a05
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096591B2

Verknüpfte Notizen

Wird geladen…