Ethylene Glycol → 8,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 2307046ノート

反応式

HRID 2307046 の反応式
C([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[C:17]([Cl:23])[C:16]([Cl:24])=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].C(O)CO>O>[Cl:24][C:16]1[C:17]([Cl:23])=[CH:18][C:19]2[C:20]3[CH2:21][CH2:22][NH:9][CH2:10][CH2:11][C:12]=3[NH:13][C:14]=2[CH:15]=1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 22503758HCID 22503758、化合物

生成物 1

HCID 226092048,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole収率 73.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
170 °C

実験手順

A mixture of 3-benzoyl-8,9-dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (2.00 g, 5.57 mmol), potassium hydroxide (3.00 g, 53.5 mmol), and ethylene glycol (15 mL) was heated to 170° C. After 2 h, the reaction was cooled to room temperature, diluted with H2O, and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with CH2Cl2/MeOH/Et2NH (9:1:0 followed by 97:3:1 followed by 95:4:1) to give 1.04 g (73%) of 8,9-dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as a dark yellow solid. 1H NMR (d-CHCl3) δ 7.75, 7.50, 7.34, 3.08, 2.92, 2.82, 1.91: MS (ESI) 255.1 (M++H).

後処理

  1. temperaturethe reaction was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography with CH2Cl2/MeOH/Et2NH (9:1:0 followed by 97:3:1 followed by 95:4:1)

出典と根拠

ORDレコード
ord-4d346d78cdb84bef8e548e12a10b835d
出典データセット
uspto-grants-2004_12
特許番号
US06828314B2

反応ノート

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