Hydrochloric Acid → Agomelatine

HRID 541492Notes

Reaction equation

HRID 541492 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:4][CH:3]=1.CC([O-])(C)C.[K+].Cl>C(O)(C)(C)C>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[CH:3][CH:4]=[C:5]2[CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 68283137HCID 68283137, compound

Product 1

HCID 82148AgomelatineYield 68%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of the compound obtained in Step C (125 mg, 0.45 mmol) in tert-butanol (1 mL) at reflux there is added potassium tert-butylate (200 mg, 1.8 mmol). The mixture is stirred for 3 hours under reflux and then hydrochloric acid (1N) is added. The aqueous phase is extracted with dichloromethane and the organic phases are washed with saturated NaCl solution, dried over magnesium sulphate, filtered and evaporated. The title compound is obtained after purification by flash column chromatography (ethyl acetate-petroleum ether: 90-10, then ethyl acetate-methanol: 90-10) in the form of a solid in a yield of 68%.

Workup

  1. temperatureunder reflux
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. washthe organic phases are washed with saturated NaCl solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b6f08b9da27e4d6cbed4537a3a2841d7
Source dataset
uspto-grants-2014_10
Patent number
US08871975B2

Reaction notes

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