Hydrogen Bromide → AGN-PC-0NGP71

HRID 239728Notes

Reaction equation

HRID 239728 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11]C)[CH2:6][NH2:7].[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1.Br>CC(=O)CC>[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH2:6][NH:7][CH2:14][CH2:13][CH2:19][S:16]([OH:18])(=[O:17])=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14264Propane sultoneHCID 79832Veratrylamine

Product 1

HCID 11149660AGN-PC-0NGP71

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3,4-dimethoxybenzylamine (2.2 mL, 15.0 mmol) in 2-butanone (20 mL) was added 1,3-propane sultone (1.98 g, 15.8 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2×25 mL) and dried in vacuo. The crude product was suspended in 75% Acetone/MeOH (75 mL). The suspension was stirred at reflux for 30 sec.; the solid material was collected by filtration, washed with acetone (2×25 mL), and dried in vacuo. The solid (1.94 g, 6.7 mmol) was dissolved hydrobromic acid (48%, 27 mL). The solution was stirred at 100° C. for 4 h. The solvent was removed under reduced pressure. The residue was dissolved in water (20 mL). The aqueous phase was washed with CH2Cl2 (3×20 mL), and evaporated under educed pressure. The solid residue was suspended in hot MeOH (75 mL). The suspension was stirred at reflux for 30 sec.; the solid was collected by filtration, washed with 50% MeOH/acetone, and dried in vacuo. This allowed the isolation of compound S, 1.22 g (70%).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in vacuo
  5. stirringThe suspension was stirred
  6. temperatureat reflux for 30 sec
  7. filtrationthe solid material was collected by filtration
  8. washwashed with acetone (2×25 mL)
  9. customdried in vacuo
  10. stirringThe solution was stirred at 100° C. for 4 h
  11. customThe solvent was removed under reduced pressure
  12. dissolutionThe residue was dissolved in water (20 mL)
  13. washThe aqueous phase was washed with CH2Cl2 (3×20 mL)
  14. customevaporated under educed pressure
  15. stirringThe suspension was stirred
  16. temperatureat reflux for 30 sec
  17. filtrationthe solid was collected by filtration
  18. washwashed with 50% MeOH/acetone
  19. customdried in vacuo

Sources & evidence

ORD record
ord-a1dd76e014d645618bfabc31bb25c7e4
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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