Citric Acid → HCID 131733671, compound

HRID 1754626Notes

Reaction equation

HRID 1754626 reaction equation
[CH3:1][N:2]1[CH2:19][CH:18]2[CH:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[O:11][C:12]3[CH:13]=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=32)[CH2:3]1.[C:21]([OH:33])(=[O:32])[CH2:22][C:23]([CH2:28][C:29]([OH:31])=[O:30])([C:25]([OH:27])=[O:26])[OH:24]>CC(C)=O.O>[CH3:1][N:2]1[CH2:19][CH:18]2[CH:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[O:11][C:12]3[CH:13]=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=32)[CH2:3]1.[C:21]([O-:33])(=[O:32])[CH2:22][C:23]([CH2:28][C:29]([O-:31])=[O:30])([C:25]([O-:27])=[O:26])[OH:24]

Participants

5

Reactant 2

HCID 311Citric Acid2×HCID 99039705-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrrole2×

Product 1

HCID 131733671HCID 131733671, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

150 mg Asenapine free base was dissolved in 3.0 ml acetone and to this solution was added 0.25 ml of a 2M stock solution of citric acid (Fluka #24788) in water. After seeding with a few of crystalline citrate salt according to example 1 a white suspension begins to form after 5 minutes. Stirring was continued at room temperature, and on the next day the suspension was filtered and the product dried under vacuum at room temperature for about 18 hours. The obtained sample was characterized by powder X-ray diffraction, which confirmed that the same crystalline form as in example 1 was obtained. Further investigation by elemental composition analysis showed a composition that is consistent with a 1:1 salt of Asenapine and citric acid as provided in Table 2. Differential scanning calorimetry shows a single melting peak at 174° C. with an enthalpy of fusion of about 116 J/g.

Workup

  1. customto form after 5 minutes
  2. customwas continued at room temperature
  3. filtrationon the next day the suspension was filtered
  4. customthe product dried under vacuum at room temperature for about 18 hours
  5. customwas obtained
  6. customas provided in Table 2
  7. customat 174° C.

Sources & evidence

ORD record
ord-b438608ba0c04ef8b2ca023952dcc700
Source dataset
uspto-grants-2015_10
Patent number
US09169262B2

Reaction notes

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