Benzoic Acid → HCID 178422259, compound

HRID 2373150Notes

Reaction equation

HRID 2373150 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:14]=[C:15]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)[C:4]=2[CH:3]=1.[C:23]([OH:31])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)(=O)C>[CH3:1][C:2]1[S:6][C:5]2[C:4](=[C:15]([N:16]3[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]3)[NH:14][C:13]3[C:8]([N:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:3]=1.[CH:27]1[CH:28]=[CH:29][C:24]([C:23]([OH:31])=[O:30])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 243Benzoic Acid2×HCID 135398745Olanzapine2×

Product 1

HCID 178422259HCID 178422259, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a clear solution (50° C.) of 100 g olanzapine free base in 2000 ml ethyl acetate, was added slowly a clear solution of 39.2 g benzoic acid in 250 ml ethyl acetate while stirring mechanically. When almost all benzoic acid was added, the crystallization process started (T=50-55° C.). The mixture was allowed to cool to room temperature while stirring. The pale yellow crystals were isolated by filtration and dried overnight at 40° C. in vacuum. Isolated yield: 130.1 gram (94%). 1H-NMR confirms the molar ratio of olanzapine:acid=1:1. DSC: peak at 222.99° C.

Workup

  1. custom(T=50-55° C.)
  2. stirringwhile stirring
  3. customThe pale yellow crystals were isolated by filtration
  4. customdried overnight at 40° C. in vacuum
  5. customIsolated yield: 130.1 gram (94%)
  6. customat 222.99° C.

Sources & evidence

ORD record
ord-6237dd45be50410bb32ecfa836607e1d
Source dataset
uspto-grants-2008_12
Patent number
US07459449B2

Reaction notes

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