Hydrogen Bromide → Galantamine Hydrobromide

HRID 907407

Reaction equation

HRID 907407 reaction equation
[CH3:1][N:2]1[CH2:20][C:14]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:12]3[C:13]=2[C@:5]2([C@@H:10]([O:11]3)[CH2:9][C@@H:8]([OH:21])[CH:7]=[CH:6]2)[CH2:4][CH2:3]1.[BrH:22]>C(O)C>[CH3:1][N:2]1[CH2:20][C:14]2=[C:13]3[C:12](=[C:17]([O:18][CH3:19])[CH:16]=[CH:15]2)[O:11][C@@H:10]2[C@:5]3([CH:6]=[CH:7][C@H:8]([OH:21])[CH2:9]2)[CH2:4][CH2:3]1.[BrH:22]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 9651(-)-Galantamine

Product 1

HCID 121587Galantamine Hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Total alkaloids (3.5 kg) containing 40% galanthamine, obtained according to example 1, are dissolved in 20 l of 95% ethanol. The solution is cooled to 0° C. and added under stirring with 2.1 l of 48% aqueous hydrobromic acid, keeping the temperature during the addition between 0 and 5° C. The mixture is left under stirring at room temperature for four hours, the product is recovered by filtration, washed with 95% ethanol and dried under vacuum at 60° C. 2.22 kg of galanthamine hydrobromide having HPLC purity of 88% are obtained. The filtration mother liquors, which contain traces of galanthamine hydrobromide, are removed.

Workup

  1. customobtained
  2. additionadded
  3. additionduring the addition between 0 and 5° C
  4. waitThe mixture is left
  5. filtrationthe product is recovered by filtration
  6. washwashed with 95% ethanol
  7. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-f6cbb5e78d624fdcbc6615ef089d9f2f
Source dataset
uspto-grants-2011_09
Patent number
US08013151B2

Linked notes

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