Flupirtine → Flupirtine maleate

HRID 1514664Notes

Reaction equation

HRID 1514664 reaction equation
[CH3:1][CH2:2][O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[N:11][C:12]=1[NH2:13])=[O:5].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27]>C(O)(C)C>[CH3:1][CH2:2][O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[N:11][C:12]=1[NH2:13])=[O:5].[CH:24](/[C:23]([OH:30])=[O:29])=[CH:25]/[C:26]([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 53276Flupirtine3×HCID 444266Maleic Acid2×

Product 1

HCID 6435335Flupirtine maleateYield 99.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
20 °C

Procedure

30 g of Flupirtine base were dissolved in 1080 ml of isopropanol at 50° C. 12.8 g of Maleic acid was dissolved in 96 ml of isopropanol at 20° C. Flupirtine solution was cooled down to 20° C. Maleic acid solution was added to Flupirtine solution in the course of stirring. The sediment was formed almost at once. The mixture was heated and stirred for 60 min at 60° C. Then the mixture was cooled down to 20° C. The sediment was filtered and washed three times with cooled (0° C.) Isopropanol. The sediment formed was white. 41.4 g of the product was formed.

Workup

  1. customThe sediment was formed almost at once
  2. temperatureThe mixture was heated
  3. stirringstirred for 60 min at 60° C
  4. filtrationThe sediment was filtered
  5. washwashed three times
  6. temperaturewith cooled (0° C.) Isopropanol
  7. customThe sediment formed

Sources & evidence

ORD record
ord-fe41a309beb042a5bfeba9a009b3affe
Source dataset
uspto-grants-2012_07
Patent number
US08222282B2

Reaction notes

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