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

HRID 2307046노트

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HRID 2307046 반응식
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

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 22503758HCID 22503758, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
170 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4d346d78cdb84bef8e548e12a10b835d
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828314B2

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