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

Reaction equation

HRID 452387 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0645b7de7a584988bbc1b42f787075b2
Source dataset
uspto-grants-2013_07
Patent number
US08492373B2

Linked notes

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