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Phenethyl bromide → 10,11-dihydro-5-methyl-10-(2-phenylethyl)-5H-pyrido-[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

HRID 982327
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 982327
[Mg].BrCCBr.Br[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:15][N:16]1[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:21]=2[N:20]=[CH:19][C:18]2=[CH:27][CH:28]=[CH:29][N:17]12.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH3:15][N:16]1[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:21]=2[NH:20][CH:19]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:18]2=[CH:27][CH:28]=[CH:29][N:17]12
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Komponenten

8

Edukt 5

HCID 7666Phenethyl bromideHCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 146019475-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

Produkt 1

HCID 1460195310,11-dihydro-5-methyl-10-(2-phenylethyl)-5H-pyrido-[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 2.8 g of magnesium turnings in 20 ml of diethyl ether and 20 ml of tetrahydrofuran was added 1 ml of 1,2-dibromoethane followed by 13.94 ml of 2-bromoethylbenzene (dropwise). After initiating the reaction with external heat, the mixture was stirred at room temperature for one hour and then treated, dropwise, with a solution of 10.0 g of 5-methyl-5H-pyrido[3,4-f]-pyrrolo[1,2-b][1,2,5]triazepine in 100 ml of tetrahydrofuran. The reaction mixture was then stirred at room temperature for two hours, poured into an iced ammonium chloride solution, stirred for five minutes, and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate). Flash chromatography of the resultant oil (silica gel; elution with 10% methanol/dichloromethane) afforded a solid which was recrystallized from diethyl ether/ethyl acetate (10:1) to yield 1.25 g of 10,11-dihydro-5-methyl-10-(2-phenylethyl)-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine, mp 92°-94° C.

Aufarbeitung

  1. customthe reaction with external heat
  2. additiontreated
  3. stirringThe reaction mixture was then stirred at room temperature for two hours
  4. stirringstirred for five minutes
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)
  11. washFlash chromatography of the resultant oil (silica gel; elution with 10% methanol/dichloromethane)
  12. customafforded a solid which
  13. customwas recrystallized from diethyl ether/ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-b8683c377122420e835558b431fbb90a
Quelldatensatz
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04996205

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