Sodium Iodide → HCID 14881416, compound

HRID 1460684Notes

Reaction equation

HRID 1460684 reaction equation
[C:1]1([CH:7]([C:15]#[N:16])[CH2:8][CH2:9]CS([O-])(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[Na+].[ClH:19].[N:20]1([C:26]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[NH:34][C:33](=[O:38])[CH2:32][CH2:31]3)=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(N(CC)CC)C>[ClH:19].[C:15]([CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][CH2:9][N:23]1[CH2:24][CH2:25][N:20]([C:26]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[NH:34][C:33](=[O:38])[CH2:32][CH2:31]3)=[O:27])[CH2:21][CH2:22]1)#[N:16]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 13195343HCID 13195343, compoundHCID 131716210HCID 131716210, compound

Product 1

HCID 14881416HCID 14881416, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3.8 Grams of 3-phenyl-3-cyanopropylmesylate was dissolved in 60 ml of dimethylformamide, then to this solution was added 4.0 g of sodium iodide and stirred at 60° C. to 70° C. for 30 minutes. Next, 5.8 g of 6-(1-piperazinylcarbonyl)-3,4-dihydrocarbostyril hydrochloride and 5.5 ml of triethylamine were added thereto and heated at 70° C. to 80° C. for 5 hours. The solvent was removed by evaporation, to the residue thus obtained was added 5%-potassium carbonate aqueous solution, then the mixture was extracted with chloroforom. The extract was washed with water, and an aqueous solution saturated with sodium chloride, and dried with magnesium sulfate. After removal of the solvent by evaporation, the residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane →dichloromethane:methanol =100:5), then the desired product was converted into a hydrochloride, recrystallized from ethanol-water to yield 2.0 g of 6-[4-(3-cyano-3-phenylpropyl)-1-piperazinylcarbonyl] -3,4-dihydrocarbostyril monohydrochloride. Colorless powdery substance. Melting point: 249° C.-251° C. (decomp.).

Workup

  1. temperatureheated at 70° C. to 80° C. for 5 hours
  2. customThe solvent was removed by evaporation, to the residue
  3. customthus obtained
  4. extractionthe mixture was extracted with chloroforom
  5. washThe extract was washed with water
  6. dry with materialan aqueous solution saturated with sodium chloride, and dried with magnesium sulfate
  7. customAfter removal of the solvent
  8. customby evaporation
  9. customthe residue thus obtained
  10. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane →dichloromethane:methanol =100:5)
  11. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-430f3c6b9eff4c89b7d04d3b372d77eb
Source dataset
uspto-grants-1991_12
Patent number
US05071856

Reaction notes

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