Potassium Iodide → Ocaperidone

HRID 374768Notes

Reaction equation

HRID 374768 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:7]2=[N:6][C:5]=1[CH3:16].Cl.[F:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[N:24][O:25][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([CH:26]3[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][C:4]4[C:9](=[O:10])[N:8]5[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:7]5=[N:6][C:5]=4[CH3:16])[CH2:30][CH2:31]3)=[N:24][O:25][C:21]=2[CH:20]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11334359R-56109 hydrochlorideHCID 18995805HCID 18995805, compound

Product 1

HCID 71351OcaperidoneYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.8 parts of 3-(2-bromoethyl)-2,9-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one, 3.9 parts of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole monohydrochloride, 10 parts of sodium carbonate, a few crystals of potassium iodide and 144 parts of 4-methyl-2-pentanone was stirred overnight at room temperature. After cooling, the reaction mixture was poured into water. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was crystallized from acetonitrile, yielding 3 parts (47.6%) of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-2,9-dimethyl-4H-pyrido[1,2-a]-pyrimidin-4-one; mp. 199.9° C. (comp. 1).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5)
  7. customThe eluent of the desired fraction was evaporated
  8. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-97613a49ed404f53a6434082a6e6852a
Source dataset
uspto-grants-1996_01
Patent number
US05482943

Reaction notes

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