Ethylene Glycol → HCID 22396945, compound

HRID 1370468Notes

Reaction equation

HRID 1370468 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[O:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]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.[NH4+].[OH-]>O.CO.C(Cl)(Cl)Cl>[CH:30]1([O:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[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)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 22396844HCID 22396844, compound

Product 1

HCID 22396945HCID 22396945, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

The 3-benzoyl-10-[2-(cyclopentyloxy)phenyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.73 g, 1.6 mmol), potassium hydroxide (2.07 g, 32.1 mmol), and ethylene glycol (15 mL) were heated to 170° C. for 2.67 hours. The reaction was diluted with water and extracted with ethyl acetate (2×). The organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo to give a brown oil which was passed through a column of silica gel with 3% methanol/chloroform with 1% NH4OH to give 419 mg (74%) of a white foam as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.83 (br s, 1H), 7.35-7.26 (m, 3H), 7.15-7.11 (m, 1H), 7.03-6.96 (m, 2H), 6.91 (d, J=7.2 Hz, 1H), 4.69-4.65 (m, 1H), 3.11-3.07 (m, 2H), 2.99-2.95 (m, 2H), 2.87-2.81 (m, 2H), 2.45-2.39 (m, 2H), 1.73-1.67 (m, 4H), 1.48-1.45 (m, 4H); HRMS (FAB) calcd for C23H26N2O+H1: 347.2123 found 321.2134.

Workup

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

Sources & evidence

ORD record
ord-f4c9b54dcd3145248e73f66066383b70
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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