Water → 6-[3-(1,3-Dimethyl-3-cyclohexylureido)propoxy]carbostyril

HRID 1856767Notes

Reaction equation

HRID 1856767 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.[CH3:18][N:19]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:20](Cl)=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2)[C:20]([N:19]([CH3:18])[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130557376-(3-Methylaminopropoxy)carbostyrilHCID 15209947N-cyclohexyl-N-methylcarbamoyl chloride

Product 1

HCID 221326006-[3-(1,3-Dimethyl-3-cyclohexylureido)propoxy]carbostyrilYield 47.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(3-Methylaminopropoxy)carbostyril (3 g) is dissolved in dimethylformamide (150 ml), and thereto are added N-methyl-N-cyclohexylaminocarbonyl chloride (2.3 g) and potassium carbonate (2 g). The mixture is stirred at room temperature overnight, and further heated with stirring at 80° C. for 2 hours. The reaction solution is poured into water, and extracted with ethyl acetate. The extract is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=30:1), and recrystallized from ethyl acetate to give 6-[3-(1,3-dimethyl-3-cyclohexylureido)propoxy]carbostyril (2.3 g) as a white powder.

Workup

  1. temperaturefurther heated
  2. stirringwith stirring at 80° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract is concentrated under reduced pressure
  5. customto remove the solvent
  6. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=30:1)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-538431f7e53e4cb299e9d71d87f0aff1
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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