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

HRID 1071133ノート

反応式

HRID 1071133 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21584188Chloroform methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba9de0adff5745ab98a42885abfc37db
出典データセット
uspto-grants-2005_06
特許番号
US06903090B2

反応ノート

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