Hydrogen Bromide → Desacetyl-7-desmethyl Agomelatine Hydrobromide

HRID 52290Notes

Reaction equation

HRID 52290 reaction equation
Cl.C[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.[BrH:17]>>[BrH:17].[OH: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

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 160500552-(7-Methoxynaphthalen-1-yl)ethan-1-amine hydrochloride

Product 1

HCID 18007945Desacetyl-7-desmethyl Agomelatine HydrobromideYield 80%

Procedure

13.8 g (5.81×10-2 mol) of 2-(7-methoxy-1-naphthyl)ethylamine hydrochloride and 46 cm3 of 47% hydrobromic acid solution are introduced into a 250-cm3 round- bottom flask with a ground neck. The mixture is brought to reflux for 6.5 hours. After cooling, the reaction medium is filtered. The precipitate is washed with water and then with hexane. Recrystallization of the crude product is carried out in an ethyl acetate/hexane mixture to obtain 2-(7-hydroxy-l-naphthyl)ethylamine hydrobromide (yield 80%; melting point: 174°-175° C.).

Workup

  1. temperatureto reflux for 6.5 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction medium is filtered
  4. washThe precipitate is washed with water
  5. customRecrystallization of the crude product

Sources & evidence

ORD record
ord-ecf2d3c84539444dac01d1c5b527fef9
Source dataset
uspto-grants-1997_04
Patent number
US05616614

Reaction notes

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