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Sodium Bicarbonate → 1-(2,4-dichlorophenyl)-4-(4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

HRID 23546
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 23546
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:28])=[CH:16][C:17]([N:18]3[CH2:27][CH2:26][C:21]4(OCC[O:22]4)[CH2:20][CH2:19]3)=[C:12]2[C:11]([CH3:29])=[C:10]1[CH3:30].C(=O)([O-])O.[Na+]>Cl.O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:28])=[CH:16][C:17]([N:18]3[CH2:27][CH2:26][C:21](=[O:22])[CH2:20][CH2:19]3)=[C:12]2[C:11]([CH3:29])=[C:10]1[CH3:30]
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Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 12134654HCID 12134654, Verbindung

Produkt 1

HCID 121346551-(2,4-dichlorophenyl)-4-(4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridineAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

After 1-(2,4-dichlorophenyl)-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]-pyridine (5.21 g) was stirred in a mixture of 4 M hydrochloric acid (60 mL) and tetrahydrofuran (60 mL) at room temperature for 2.5 hours, 6 M hydrochloric acid (30 mL) was added thereto and the resulting mixture was stirred overnight. After completion of the reaction, the reaction mixture was poured into a saturated aqueous sodium hydrogen-carbonate solution and extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, after which the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The crystals thus obtained were washed with ethyl acetate to obtain 1-(2,4-dichlorophenyl)-4-(4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (3.83 g).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationafter which the desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crystals thus obtained
  7. washwere washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-caac4ca01fad401d8a0672d766d57787
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06852732B2

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