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

HRID 382318Notes

Reaction equation

HRID 382318 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 the boron tribromide/dimethyl sulphide complex are dissolved in 100 ml of dichloromethane and stirred for 15 minutes at room 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 refluxed for 30 hours. After cooling, the reaction mixture is hydrolysed cautiously and the dichloromethane is removed by evaporation. The mixture is then extracted with ethyl acetate, and the combined organic phases are washed with an aqueous 1M potassium hydrogen carbonate solution. The organic phase is dried over magnesium sulphate and concentrated to yield the title compound. White solid.

Workup

  1. temperaturethe reaction mixture is refluxed for 30 hours
  2. temperatureAfter cooling
  3. customthe dichloromethane is removed by evaporation
  4. extractionThe mixture is then extracted with ethyl acetate
  5. washthe combined organic phases are washed with an aqueous 1M potassium hydrogen carbonate solution
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-42bef7153720409b8d122efc610e8513
Source dataset
uspto-grants-2001_10
Patent number
US06310074B1

Reaction notes

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