Diethyl Ether → HCID 72727347, compound

HRID 477187Notes

Reaction equation

HRID 477187 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([OH:3])=O.C1(N=C=NC2CCCCC2)CCCCC1.[OH:30][N:31]=[C:32]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.CCOCC>O1CCOCC1.C(Cl)(Cl)Cl>[OH:30][N:31]=[C:32]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:33][CH2:34][N:35]1[CH2:36][CH2:37][N:38]([C:1]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3)=[O:3])[CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acidHCID 85555412HCID 85555412, compound

Product 1

HCID 72727347HCID 72727347, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

One gram of 6-carboxy-3,4-dihydrocarbostyril, 1.3 g of dicyclohexylcarbodiimide and 1.47 g of (3-hydroxyimino-3-phenylpropyl)piperazine were suspended in 10 ml of dioxane, then the suspension was stirred at 60° to 70° C. for 5 hours. After the reaction was completed, the solvent was removed by evaporation, to the residue thus obtained was added ether so as to form crystals, then the crystals were removed by filtration. The mother liquor was concentrated, then the residue thus obtained was dissolved by adding chloroform, and the solution was washed with water and an aqueous solution saturated with sodium chloride, then dried with anhydrous potassium carbonate, and the solvent was removed by evaporation. The residue thus obtained was recrystallized from ethanol to yield 320 mg of 6-[4-(3-hydroxyimino-3-phenylpropyl)-1-piperazinylcarbonyl]3,4-dihydrocarbostyril.semihydrate. White powdery substance.

Workup

  1. customthe solvent was removed by evaporation, to the residue
  2. customthus obtained
  3. customto form crystals
  4. customthe crystals were removed by filtration
  5. concentrationThe mother liquor was concentrated
  6. customthe residue thus obtained
  7. dissolutionwas dissolved
  8. washthe solution was washed with water
  9. dry with materialan aqueous solution saturated with sodium chloride, then dried with anhydrous potassium carbonate
  10. customthe solvent was removed by evaporation
  11. customThe residue thus obtained
  12. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c60df941562442b49acb84b440ba823d
Source dataset
uspto-grants-1989_12
Patent number
US04886809

Reaction notes

Loading…