Sodium Iodide → 2(1H)-Quinolinone, 3,4-dihydro-6-(1-oxo-3-(4-(phenylmethyl)-1-piperidinyl)propyl)-

HRID 1285461Notes

Reaction equation

HRID 1285461 reaction equation
[O:1]=[C:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2)[CH2:3][CH2:4]Cl.[I-].[Na+].[CH2:19]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCN2C(=NCCC2)CC1.C(=O)([O-])O.[Na+]>C(O)(C)C>[O:1]=[C:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2)[CH2:3][CH2:4][N:29]1[CH2:30][CH2:31][CH:26]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27][CH2:28]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 317384-BenzylpiperidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 12833509HCID 12833509, compound

Product 1

HCID 30670982(1H)-Quinolinone, 3,4-dihydro-6-(1-oxo-3-(4-(phenylmethyl)-1-piperidinyl)propyl)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.4 Grams of 6-(1-oxo-3-chloropropyl)-3,4-dihydrocarbostyril and 1.6 g of sodium iodide were mixed in 60 ml of isopropanol and stirred at 40°-50° C. for 2 hours. Then 2.2 g of 4-benzylpiperidine and 3.0 g of DBU were added to the reaction mixture and refluxed by heating for 6 hours. The reaction mixture was poured into 100 ml of 5%-sodium hydrogen-carbonate aqueous solution and stirred at a room temperature for 1 hour. The insoluble matters fromed were collected by filtration washed with water and dried, then recrystallized from ethanol to obtain 1.8 g of 6-[1-oxo-3-(4-benzyl-1-piperidyl)propyl]-3,4-dihydrocarbostyril in light yellow plate-like crystals.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 6 hours
  3. stirringstirred at a room temperature for 1 hour
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8bd36598935c4b77ad0490f23d3a4a29
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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