Reaction #2460331

ord-97d95bd667104b48b84532079254b46d

Reaction equation

O=C(O)c1ccccc1
benzoic acid
Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1
olanzapine
Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1
olanzapine
→
Cc1cc2c(s1)=Nc1ccccc1NC=2N1CCN(C)CC1.O=C(O)c1ccccc1
Olanzapine Benzoate

Reactants

O=C(O)c1ccccc1
benzoic acid
Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1
olanzapine
Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1
olanzapine

Reagents

None

Solvents

CCOC(C)=O
ethyl acetate
CCOC(C)=O
ethyl acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONAfter complete addition
  2. 2
    OtherThe crystals were isolated by filtration
  3. 3
    Otherdried overnight at 50° C. in vacuo
  4. 4
    OtherIsolated yield: 0.64 gram (92%)

Procedure

To a clear solution of 0.196 g benzoic acid in 5 ml ethyl acetate was added slowly a clear hot solution of 0.5 g olanzapine free base in 10 ml ethyl acetate. After complete addition, slowly, the crystallization process started. Stirring at room temperature was continued for 5 hours. The crystals were isolated by filtration and dried overnight at 50° C. in vacuo. Isolated yield: 0.64 gram (92%). 1H-NMR confirmed the molar ratio olanzapine: acid=1:1.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07459449B2uspto-grants-2008_12