Ethylene Glycol → 10-(2-Fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1071133노트

반응식

HRID 1071133 반응식
C([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])=[CH:17][CH:16]=[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.[NH4+].[OH-]>O.CO.C(Cl)(Cl)Cl>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:18]1[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]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 223966933-Benzoyl-10-(2-fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

생성물 1

HCID 2239670010-(2-Fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

시약·촉매·용매 2

HCID 962Water용매HCID 21584188Chloroform methanol용매

실험 절차

3-Benzoyl-10-(2-fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (3.50 g, 9.1 mmol), potassium hydroxide (11.80 g, 183 mmol), and ethylene glycol (80 mL) were heated to 170° C. for 6.6 hours. The reaction was diluted with water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo to give a red oil which was passed through a column of silica gel with 1:19 methanol/chloroform with 1% NH4OH to give 2.43 g (95%) of a white solid as the title compound: mp 121.8-126.3° C. 1H NMR (400 MHz, CDCl3) δ 8.02 (br s, 1H), 7.42-7.34 (m, 3H), 7.26-7.16 (m, 3H), 6.98 (d, J=7.2 Hz, 1H), 3.16-2.86 (m, 6H), 2.58-2.53 (m, 1H), 2.46-2.39 (m, 1H); MS m/z 281.2 (M++H).

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a red oil which

출처 및 근거

ORD 기록
ord-ba9de0adff5745ab98a42885abfc37db
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903090B2

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