Water → Agomelatine

HRID 1782547Notes

Reaction equation

HRID 1782547 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(OC(=O)C)(=O)C.O>C(O)C>[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 962WaterHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 160500552-(7-Methoxynaphthalen-1-yl)ethan-1-amine hydrochloride

Product 1

HCID 82148AgomelatineYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

173 kg of the compound obtained in Step C and 66 kg of sodium acetate in ethanol are introduced into a 1600 liter reactor. The mixture is stirred and then 79 kg of acetic anhydride are added; the reaction mixture is heated at reflux and 600 l of water are added. The reaction mixture is allowed to return to ambient temperature and the precipitate obtained is filtered off and washed with a 35/65 ethanol/water mixture to give the title product in a yield of 92.5% and with a chemical purity exceeding 99%.

Workup

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

Sources & evidence

ORD record
ord-622244ec24d0411ab05fdf9ec7365129
Source dataset
uspto-grants-2009_03
Patent number
US07498466B2

Reaction notes

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