Sodium Iodide → HCID 18958819, compound

HRID 1708369Notes

Reaction equation

HRID 1708369 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:13])[CH2:6][CH2:5][C:3]1=[O:4].Br[CH2:15][CH2:16][CH2:17][CH2:18]Br.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl:28]CCl.O>C(#N)C>[ClH:28].[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 14627584HCID 14627584, compoundHCID 21908982Water methylene chloride

Product 1

HCID 18958819HCID 18958819, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension prepared by mixing 1 g of 1-methyl-8-amino-3,4-dihydrocarbostyril, 1.35 g of 1,4-dibromobutane, 1.9 g of sodium iodide, 1.75 g of potassium carbonate in 10 ml of acetonitrile was refluxed by heating for 20 hours. Then to the reaction mixture was added dichloromethane-water, and the organic layer was collected by separation, washed with water, and dried with anhydrous sodium sulfate. Next, the solvent was removed by evaporation, and the residue thus obtained was purified by a silica gel column chromatography (eluent: dichloromethane:methanol=50:1). The purified product was dissolved in diethyl ether, and the desired product was converted into hydrochloride by using ethanol-concentrated hydrochloric acid, recrystallized from ethanol-diethyl ether to obtain 1.15 g of 1-methyl-8-pyrrolidino-3,4-dihydrocarbostyril hydrochloride. White powdery substance. Melting point: 174.5°-177° C.

Workup

  1. customA suspension prepared
  2. temperaturewas refluxed
  3. temperatureby heating for 20 hours
  4. customthe organic layer was collected by separation
  5. washwashed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customNext, the solvent was removed by evaporation
  8. customthe residue thus obtained
  9. customwas purified by a silica gel column chromatography (eluent: dichloromethane:methanol=50:1)
  10. dissolutionThe purified product was dissolved in diethyl ether
  11. customrecrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-17ce8d74721e42b18787914452eeccb2
Source dataset
uspto-grants-1994_10
Patent number
US05358949

Reaction notes

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