Agomelatine → N-(2-(7-hydroxy-1-naphthyl)ethyl)acetamide

HRID 351136Notes

Reaction equation

HRID 351136 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 82148Agomelatine

Product 1

HCID 11775984N-(2-(7-hydroxy-1-naphthyl)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an inert atmosphere, 27.5 mmol of boron tribromide/dimethyl sulphide complex are dissolved in 100 ml of dichloromethane and stirred for 15 min at ambient temperature. A solution of 13.7 mmol of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide in 50 ml of dichloromethane is added and the reaction mixture is heated at reflux for 30 hours. After cooling, the reaction mixture is hydrolysed with caution and the dichloromethane is evaporated off. The mixture is then extracted with ethyl acetate, the combined organic phases are washed with a 1M aqueous solution of potassium bicarbonate and then with 1M sodium hydroxide solution. The organic phase is dried over magnesium sulphate and concentrated to yield the title compound.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 30 hours
  3. temperatureAfter cooling
  4. customthe dichloromethane is evaporated off
  5. extractionThe mixture is then extracted with ethyl acetate
  6. washthe combined organic phases are washed with a 1M aqueous solution of potassium bicarbonate
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b298aa0a9a394b3384f0072abf42ec42
Source dataset
uspto-grants-2007_02
Patent number
US07183318B2

Reaction notes

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