5,6,7,8,9,10-Hexahydrocycloocta[b]pyridin-2(1H)-one → 2-Chloro-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

HRID 452387

Reaktionsgleichung

Reaktionsgleichung von HRID 452387
[NH:1]1[C:6](=O)[CH:5]=[CH:4][C:3]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:2]1=2.O(Cl)[Cl:15].[P+3]>>[Cl:15][C:6]1[N:1]=[C:2]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3]2=[CH:4][CH:5]=1

Komponenten

3

Edukt 2

HCID 248085025,6,7,8,9,10-Hexahydrocycloocta[b]pyridin-2(1H)-oneHCID 178479710HCID 178479710, Verbindung

Produkt 1

HCID 581995322-Chloro-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Versuchsvorschrift

5,6,7,8,9,10-Hexahydrocycloocta[b]pyridin-2(1H)-one was heated with excess phosphorus (III) oxychloride at 100° C. for 8 h. The solvent was removed under vacuum. The residue was treated with ice and 1M aqueous potassium carbonate solution, and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. Flash chromatography on silica gel, eluting with a mixture of 96% dichloromethane and 4% methanol gave 2-chloro-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine as a brown oil; 1H NMR (CDCl3, 300 MHz) 7.32 (d, 1H), 7.06 (d, 1H), 2.92 (m, 2H), 2.74 (m, 2H), 1.79 (m, 2H), 1.69 (m, 2H), 1.38 (m, 4H) ppm; 13C NMR (CDCl3, 75 MHz) 161.86, 147.73, 140.19, 135.65, 122.26, 34.33, 32.30, 31.52, 30.83, 26.26, 26.14; MS (ES) 196/198 (M+H).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. additionThe residue was treated with ice and 1M aqueous potassium carbonate solution
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. washFlash chromatography on silica gel, eluting with a mixture of 96% dichloromethane and 4% methanol

Quellen und Nachweise

ORD-Eintrag
ord-0645b7de7a584988bbc1b42f787075b2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492373B2

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