Sodium Iodide → Aripiprazole

HRID 239004

Reaction equation

HRID 239004 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-a18fbd88147b417a889e11d3c18f357c
Source dataset
uspto-grants-2014_02
Patent number
US08642760B2

Linked notes

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