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Potassium Carbonate → HCID 14747672, compound

HRID 1609505
Notes
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Reaction equation

HRID 1609505 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[N:19]1([CH2:24][CH2:25][N:26]([CH2:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31]Cl)[CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[N:19]1([CH2:24][CH2:25][N:26]([CH2:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:27]([CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)=[O:33])[CH2:23][CH2:22][CH2:21][CH2:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 20081659HCID 20081659, compound

Product 1

HCID 14747672HCID 14747672, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 ml of dimethylformamide are added 1.73 g of 6-hydroxycarbostyril, 1.8 g of K2CO3 and 0.5 g of KI. To this mixture being stirred at 60°-70° C. is dropwise added 4.2 g of N-[2-(1-pyrrolidinyl)ethyl]-N-(5-chloropentanoyl)-cyclohexylmethylamine. Then, the mixture is stirred for 4 hours at the same temperature. The solvent is removed by evaporation. The residue is dissolved in 200 ml of chloroform and the solution is washed with diluted hydrochloric acid, a 1% aqueous sodium hydroxide solution and water in this order, and dried with anhydrous magnesium sulfate. The desiccant is removed by filtration and the filtrate is concentrated. The residue is purified by means of a silica gel column chromatography (eluent; chloroform:methanol=20:1) and recrystallized from diethyl ether to obtain 0.5 g of 6-[4-{N-[2-(1-pyrrolidinyl)ethyl]-N-cyclohexylmethylaminocarbonyl}butoxy]carbostyril.

Workup

  1. stirringThen, the mixture is stirred for 4 hours at the same temperature
  2. customThe solvent is removed by evaporation
  3. dissolutionThe residue is dissolved in 200 ml of chloroform
  4. washthe solution is washed with diluted hydrochloric acid
  5. dry with materiala 1% aqueous sodium hydroxide solution and water in this order, and dried with anhydrous magnesium sulfate
  6. customThe desiccant is removed by filtration
  7. concentrationthe filtrate is concentrated
  8. customThe residue is purified by means of a silica gel column chromatography (eluent; chloroform:methanol=20:1)
  9. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-e2107f5be29842db84d4e452a48baeee
Source dataset
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05401740

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes