Citric Acid → HCID 131733671, compound

HRID 1754627Notes

Reaction equation

HRID 1754627 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 AcidHCID 99039705-Chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo(2,3:6,7)oxepino(4,5-c)pyrrole

Product 1

HCID 131733671HCID 131733671, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

500 mg Asenapine free base (˜1.7 mmol) were dissolved in 1.0 ml acetone and 320 mg of citric acid (Fluka #24788) which was dissolved in 1.0 ml water was added to the solution containing the free base. This solution was then seeded with a few mg of crystalline citrate salt according to example 1 and to the very thin suspension 2.0 ml water was added and stirred was performed while keeping the vial open letting some acetone evaporate. On the next day the obtained suspension was filtered and about 633 mg of solid product was obtained after drying under vacuum at r.t. for about 18 hours. Powder X-ray diffraction of the obtained solid product showed that the same crystalline form as in example 1 was obtained.

Workup

  1. additionwas added to the solution
  2. additioncontaining the free base
  3. additionwas added
  4. customevaporate
  5. filtrationOn the next day the obtained suspension was filtered

Sources & evidence

ORD record
ord-7a2f6ceab71344e7aa65f7c65c7f3a22
Source dataset
uspto-grants-2015_10
Patent number
US09169262B2

Reaction notes

Loading…