Sodium Iodide → Aripiprazole

HRID 1947167Notes

Reaction equation

HRID 1947167 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[I-].[Na+].C(#N)C.[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:23][C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[N:31]1[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]3)=[CH:9][CH:8]=2)[CH2:33][CH2:32]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 8518331-(2,3-Dichlorophenyl)piperazineHCID 105420647-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 60795AripiprazoleYield 80.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 47 g of 7-(4-bromobutoxy)-3,4-dihydrocarbostyril, 35 g of sodium iodide with 600 ml of acetonitrile was refluxed for 30 minutes. To this suspension was added 40 g of 1-(2,3-dichlorophenyl)piperazine and 33 ml of triethylamine and the whole mixture was further refluxed for 3 hours. After the solvent was removed by evaporation, the residue thus obtained was dissolved in chloroform, washed with water then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue thus obtained was recrystallized from ethanol twice, to yield 57.1 g of 7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy}-3,4-dihydrocarbostyril.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe whole mixture was further refluxed for 3 hours
  3. customAfter the solvent was removed by evaporation
  4. customthe residue thus obtained
  5. washwashed with water
  6. dry with materialthen dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation
  8. customthe residue thus obtained
  9. customwas recrystallized from ethanol twice

Sources & evidence

ORD record
ord-f305d6d92fa0449bb369184710d56d88
Source dataset
uspto-grants-2013_03
Patent number
US08399469B2

Reaction notes

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