Asenapine → Asenapine Maleate

HRID 2065868

Reaction equation

HRID 2065868 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C@H:8]3[CH2:9][N:10]([CH3:12])[CH2:11][C@@H:7]3[C:6]=2[CH:20]=1.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25]>C(O)C>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C@H:8]3[CH2:9][N:10]([CH3:12])[CH2:11][C@@H:7]3[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 163091AsenapineHCID 444266Maleic Acid

Product 1

HCID 6917875Asenapine MaleateYield 84,144.102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To 91.0 g (0.32 mmol) of the purified trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenzo[2,3;6,7]-oxepino[4,5-c]pyrrole obtained in Production Example 2 there were added 310 mL of 99.5% ethanol and 40.6 g (0.35 mol) of maleic acid, and the obtained mixture was heated to 60° C. to obtain a homogeneous solution. The solution was cooled to −10° C. over a period of 18 hours. The precipitated crystals were separated off by filtration, and the crystals were washed with 45 mL of cold ethanol and dried to obtain 108.2 g of trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenzo[2,3;6,7]-oxepino[4,5-c]pyrrole maleate as a white solid. The yield was 84.6%.

Workup

  1. customto obtain a homogeneous solution
  2. temperatureThe solution was cooled to −10° C. over a period of 18 hours
  3. customThe precipitated crystals were separated off by filtration
  4. washthe crystals were washed with 45 mL of cold ethanol
  5. customdried

Sources & evidence

ORD record
ord-678290f633a8454ea83d7866956a888d
Source dataset
uspto-grants-2012_10
Patent number
US08288564B2

Linked notes

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