Ethanol → Agomelatine

HRID 1511167Notes

Reaction equation

HRID 1511167 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][NH2:16])=[CH:6][CH:5]=1.[C:17]([O-])(=[O:19])[CH3:18].[Na+].C(O)C.C(OC(=O)C)(=O)C>O>[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 160500552-(7-Methoxynaphthalen-1-yl)ethan-1-amine hydrochloride

Product 1

HCID 82148Agomelatine

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 and washed with an ethanol/water 35/65 mixture to yield the title product.

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-92b6f771319f45bcbea6a6f43a20e8f7
Source dataset
uspto-grants-2012_07
Patent number
US08212077B2

Reaction notes

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