Potassium Hydroxide → HCID 22396736, compound

HRID 1356359Notes

Reaction equation

HRID 1356359 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][C:26]([Cl:29])=[CH:25][CH:24]=4)=[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>[ClH:29].[ClH:29].[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:18]2[C:19]3[C:20]4[CH2:21][CH2:22][NH:9][CH2:10][CH2:11][C:12]=4[NH:13][C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22396989HCID 22396989, compound

Product 1

HCID 22396736HCID 22396736, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
170 °C

Procedure

3-benzoyl-10-(4-chlorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole and KOH (3.0 g) were stirred in ethylene glycol (10 ml) and the reaction mixture was heated at 170° C. for 1 h. The reaction mixture was cooled to RT, partitioned between H2O and EtOAc, separated, dried over MgSO4, filtered and concentrated. The product was dissolved in EtOAc and HCl (4 ml, 1N in Et2O) was added. The precipitate was filtered and recrystallized from EtOAc/MeOH to give the title compound as a solid: 1H NMR (DMSO-d6) δ 3.09, 3.18, 3.30, 4.48, 6.78, 7.08, 7.32, 7.38, 7.52, 9.60, 11.3. HRMS (FAB) calcd for C18H17ClN2 (MH+) 297.1158, found 297.1137.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. custompartitioned between H2O and EtOAc
  3. customseparated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe product was dissolved in EtOAc
  8. additionHCl (4 ml, 1N in Et2O) was added
  9. filtrationThe precipitate was filtered
  10. customrecrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-77494d95f328494ba2055c7b1d2049d5
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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