Ethylene Glycol → 8,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1356363Notes

Reaction equation

HRID 1356363 reaction equation
C([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[C:17]([Cl:23])[C:16]([Cl:24])=[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>O>[Cl:24][C:16]1[C:17]([Cl:23])=[CH:18][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]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 22503758HCID 22503758, compound

Product 1

HCID 226092048,9-Dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indoleYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-benzoyl-8,9-dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (2.00 g, 5.57 mmol), potassium hydroxide (3.00 g, 53.5 mmol), and ethylene glycol (15 mL) was heated to 170° C. After 2 h, the reaction was cooled to room temperature, diluted with H2O, and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with CH2Cl2/MeOH/Et2NH (9:1:0 followed by 97:3:1 followed by 95:4:1) to give 1.04 g (73%) of 8,9-dichloro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as a dark yellow solid. 1H NMR (d-CHCl3) δ 7.75, 7.50, 7.34, 3.08, 2.92, 2.82, 1.91; MS (ESI) 255.1 (M++H).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography with CH2Cl2/MeOH/Et2NH (9:1:0 followed by 97:3:1 followed by 95:4:1)

Sources & evidence

ORD record
ord-e3064fbad0364ff6a95ff43d54b4f211
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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