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

HRID 1903197Notes

Reaction equation

HRID 1903197 reaction equation
CN(C)C=O.[OH: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([O-])([O-])=O.[K+].[K+].[OH:24][CH2:25][CH2:26][N:27]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:28](=[O:33])[CH2:29][CH2:30][CH2:31]Cl>C(Cl)(Cl)Cl>[OH:24][CH2:25][CH2:26][N:27]([CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[C:28]([CH2:29][CH2:30][CH2:31][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)=[O:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 12836954N-(2-hydroxyethyl)-N-(4-chlorobutyryl)cyclohexylamine

Product 1

HCID 12866343N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramideYield 12.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into 50 ml of dimethylformamide were added 1.73 g of 6-hydroxycarbostyril, 1.8 g of K2CO3 and 0.5 g of KI. The mixture was heating at 60°-70° C. under stirring, then 3.2 g of N-(2-hydroxyethyl)-N-(4-chlorobutyryl)cyclohexylamine was added dropwise gradually thereto. After the addition operation, the reaction mixture was further stirred at the same temperature for 4 hours. Then the solvent was removed by distillation and the residue thus obtained was dissolved in 200 ml of chloroform and the chloroform layer was washed with a diluted hydrochloric acid, 1% Na OH aqueous solution and water in this order, then dried with anhydrous sodium sulfate. The drying agent was removed by filtration, and the mother liquid was concentrated, then the residue thus obtained was crystallized with petroleum ether. The crystals thus obtained was recrystallized from chloroform-petroleum ether to obtain 0.5 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril. Melting point: 165°-166° C.

Workup

  1. temperatureThe mixture was heating at 60°-70° C.
  2. stirringAfter the addition operation, the reaction mixture was further stirred at the same temperature for 4 hours
  3. customThen the solvent was removed by distillation
  4. customthe residue thus obtained
  5. washthe chloroform layer was washed with a diluted hydrochloric acid, 1% Na OH aqueous solution and water in this order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe mother liquid was concentrated
  9. customthe residue thus obtained
  10. customwas crystallized with petroleum ether
  11. customThe crystals thus obtained
  12. customwas recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-ada3bb29a2814705928669c25a3fac6b
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

Loading…