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

反応式

HRID 452387 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0645b7de7a584988bbc1b42f787075b2
出典データセット
uspto-grants-2013_07
特許番号
US08492373B2

関連ノート

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