Hydrogen Bromide → Desacetyl-7-desmethyl Agomelatine Hydrobromide

HRID 37287Notes

Reaction equation

HRID 37287 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-1-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-fd5b207a0985418fae5caa7753715d24
Source dataset
uspto-grants-1995_05
Patent number
US05420158

Reaction notes

Loading…