Dichloromethane → N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

HRID 1903193Notes

Reaction equation

HRID 1903193 reaction equation
C(Cl)Cl.[C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH:15]=[CH:14]2)([OH:6])=O.S(Cl)(Cl)=O.[OH:26][CH2:27][CH2:28][NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[OH:26][CH2:27][CH2:28][N:29]([CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH:15]=[CH:14]2)=[O:6]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 17827Ethanol, 2-(cyclohexylamino)-HCID 24386Thionyl ChlorideHCID 128663424-((2-Oxo-1,2-dihydroquinolin-6-yl)oxy)butanoic acid

Product 1

HCID 12866343N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Into 200 ml of methylene chloride was suspended 2.4 g of 6-(3-carboxypropoxy)carbostyril, and 2 ml of pyridine was added to the suspension. Then 1.4 g of thionyl chloride was added dropwise thereinto under stirring condition while the inside of the reaction vessel was kept at a temperature within the range from 0° to 20° C. After the addition operation, the reaction was continued at the same temperature for 1 hour under stirring condition. Then 2 ml of N-(2-hydroxyethyl)cyclohexylamine was added dropwise to the reaction mixture, then the reaction was continued at a room temperature for 4 hours under stirring. The reaction mixture was washed thoroughly with a K2CO3 aqueous solution, then further washed with water and a diluted hydrochloride acid, then dried with anhydrous sodium sulfate. The solvent was removed by distillation and the residue thus obtained was purified and isolated by a silica-gel column chromatography [the silica-gel used was "Wako C-200" and the solvent used was a mixture of chloroform:methanol=20:1 (V/V)] and was recrystallized from chloroform-petroleum ether. 1.2 Grams of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril was obtained as in the form of colorless needle-like crystals. Melting point: 165°-166° C.

Workup

  1. additionwas added to the suspension
  2. customwas kept at a temperature within the range from 0° to 20° C
  3. stirringunder stirring condition
  4. waitthe reaction was continued at a room temperature for 4 hours
  5. stirringunder stirring
  6. washThe reaction mixture was washed thoroughly with a K2CO3 aqueous solution
  7. washfurther washed with water
  8. dry with materiala diluted hydrochloride acid, then dried with anhydrous sodium sulfate
  9. customThe solvent was removed by distillation
  10. customthe residue thus obtained
  11. customwas purified
  12. customisolated by a silica-gel column chromatography [the silica-gel
  13. custommethanol=20:1 (V/V)] and was recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-c04a1e829caf430c93db3837397ae77f
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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