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

HRID 2406135

반응식

HRID 2406135 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1ff20716491b4d0d9c813a98a537c6e1
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809347B2

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