Ethanol → Agomelatine

HRID 1099498Notes

Reaction equation

HRID 1099498 reaction equation
[CH3:1][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][NH2:15])=[CH:5][CH:4]=1.[C:16]([O-])(=[O:18])[CH3:17].[Na+].C(O)C.C(OC(=O)C)(=O)C>O>[CH3:1][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

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 110526677-Methoxy-1-naphthaleneethanamine

Product 1

HCID 82148AgomelatineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reactor, 5 g of the compound obtained in Step C and 2 g of sodium acetate are introduced into ethanol. The mixture is stirred, 2.3 g of acetic anhydride are then added, the reaction mixture is heated to reflux and 20 ml of water are added. The reaction mixture is allowed to return to ambient temperature and the precipitate obtained is filtered off, washed with an ethanol/water 35/65 mixture to yield the title product in a yield of 80% with a chemical purity of 99%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux
  3. customto return to ambient temperature
  4. customthe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with an ethanol/water 35/65 mixture

Sources & evidence

ORD record
ord-27d0ddaa63ee43a487b251822d7c7b6b
Source dataset
uspto-grants-2012_03
Patent number
US08143449B2

Reaction notes

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