Hexamethylenetetramine → 2-Amino-1-(5-chloro-2-methoxy-phenyl)-ethanone hydrochloride

HRID 1616583Notes

Reaction equation

HRID 1616583 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][CH3:13])=[O:4].C1N2CN3CN(C2)C[N:15]1C3>C(Cl)(Cl)Cl>[ClH:11].[NH2:15][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][CH3:13])=[O:4]

Participants

4

Reactant 2

HCID 4101HexamethylenetetramineHCID 19891882-Bromo-1-(5-chloro-2-methoxyphenyl)ethanone

Product 1

HCID 684951822-Amino-1-(5-chloro-2-methoxy-phenyl)-ethanone hydrochlorideYield 143.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 2-bromo-1-(5-chloro-2-methoxy-phenyl)-ethanone (17.07 g, 64.78 mmol) in 150 mL of CHCl3 and add hexamethylenetetramine (9.09 g, 64.84 mmol) to the reaction mixture. Allow the reaction to stir at ambient temperature for 23 hours. Collect the solids via filtration and wash the solids with Et2O. Slurry the solid in 100 mL of MeOH and add 50 mL of concentrated HCl to it dropwise. Heat the reaction to reflux and allow it to stir for 23 hours. Cool the reaction to ambient temperature and filter off the solids. Slurry the filtrate in MeOH and again collect the solids via filtration. Concentrate the filtrate to afford 10.99 g of 2-amino-1-(5-chloro-2-methoxy-phenyl)-ethanone hydrochloride.

Workup

  1. customthe reaction
  2. customCollect the solids
  3. filtrationvia filtration
  4. washwash the solids with Et2O
  5. additionadd 50 mL of concentrated HCl to it dropwise
  6. temperatureHeat
  7. customthe reaction
  8. temperatureto reflux
  9. stirringto stir for 23 hours
  10. temperatureCool
  11. customthe reaction to ambient temperature
  12. filtrationfilter off the solids
  13. customSlurry the filtrate in MeOH and again collect the solids
  14. filtrationvia filtration
  15. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-e29d2851b2ef4a598e2411da6cb49103
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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