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

HRID 1071133Notes

Reaction equation

HRID 1071133 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ba9de0adff5745ab98a42885abfc37db
Source dataset
uspto-grants-2005_06
Patent number
US06903090B2

Reaction notes

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