Ethanol, 2-(cyclohexylamino)- → N-Cyclohexyl-N-(2-hydroxyethyl)-4-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]butanamide

HRID 1903187Notes

Reaction equation

HRID 1903187 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2)([OH:3])=O.ClC(OCC(C)C)=O.[OH:27][CH2:28][CH2:29][NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(Cl)(Cl)Cl>[OH:27][CH2:28][CH2:29][N:30]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2)=[O:3]

Participants

5

Reactant 3

HCID 17827Ethanol, 2-(cyclohexylamino)-HCID 62365Isobutyl chloroformateHCID 12819271HCID 12819271, compound

Product 1

HCID 131164N-Cyclohexyl-N-(2-hydroxyethyl)-4-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]butanamideYield 55.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into 100 ml of chloroform were added 2.5 g of 6-(3-carboxypropoxy)-3,4-dihydrocarbostyril and 1.65 g of 1,8-diazabicyclo[5,4,0]undecene-7. The outside of the reaction vessel containing the above mentioned mixture was ice-cooled and 1.5 ml of isobutyl chloroformate was added dropwise to the mixture under stirring condition. After the addition operation, stirring was continued for 30 minutes and 2.0 g of N-(2-hydroxyethyl)cyclohexylamine was added to the reaction mixture and further stirred at a room temperature for 2 hours. After the reaction was completed, the chloroform solution of the reaction product was washed with a diluted NaHCO3 aqueous solution, a diluted hydrochloric acid and water in this order. The chloroform solution was dried with anhydrous Na2SO4, then the chloroform was removed by distillation and the residue thus obtained was recrystallized from chloroform-petroleum ether to obtain 2.1 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. Melting point: 139°-141.5° C.

Workup

  1. additionThe outside of the reaction vessel containing the
  2. temperaturecooled
  3. stirringAfter the addition operation, stirring
  4. stirringfurther stirred at a room temperature for 2 hours
  5. washthe chloroform solution of the reaction product was washed with a diluted NaHCO3 aqueous solution
  6. dry with materialThe chloroform solution was dried with anhydrous Na2SO4
  7. customthe chloroform was removed by distillation
  8. customthe residue thus obtained
  9. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-9b788c9f89fb49f4beb4d5729b1fca86
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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