Ethylene Glycol → HCID 22396945, compound

HRID 2307033Notes

Reaction equation

HRID 2307033 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 (233). 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, 1 H), 7.35-7.26 (m, 3 H), 7.15-7.11 (m, 1 H), 7.03-6.96 (m, 2 H), 6.91 (d, J=7.2 Hz, 1 H), 4.69-4.65 (m, 1 H), 3.11-3.07 (m, 2 H), 2.99-2.95 (m, 2 H), 2.87-2.81 (m, 2 H), 2.45-2.39 (m, 2 H), 1.73-1.67 (m, 4 H), 1.48-1.45 (m, 4 H); HRMS (FAB) calcd for C23H26N2O+H1: 347.2123 found 321.2134.

Workup

  1. extractionextracted with ethyl acetate (233)
  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-4bf1e87660cc4bb2a5b9f31fa489c420
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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