Hydrochloric Acid → 6-(4-Geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril hydrochloride

HRID 231105Notes

Reaction equation

HRID 231105 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.[CH2:30]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)/[CH:31]=[C:32](/[CH2:34][CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])\[CH3:33].[ClH:46]>O1CCOCC1.C(O)C.C(Cl)(Cl)Cl.C(OCC)C>[ClH:46].[CH2:30]([N:40]1[CH2:41][CH2:42][N:43]([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])[CH2:44][CH2:45]1)/[CH:31]=[C:32](/[CH2:34][CH2:35][CH:36]=[C:37]([CH3:38])[CH3:39])\[CH3:33]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10868DicyclohexylcarbodiimideHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acidHCID 14497703Geranylpiperazine

Product 1

HCID 200345276-(4-Geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril hydrochloride

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

1.0 Gram of 6-carboxy-3,4-dihydrocarbostyril, 1.3 g of DCC (dicyclohexylcarbodiimide) and 1.4 g of geranylpiperazine were suspended in 10 ml of dioxane, and the suspension was stirred at 60°-70° C. for 5 hours. After the reaction was finished, the solvent was removed from the reaction mixture by evaporation, then to the residue thus obtained was added a certain amount of diethyl ether and the crystals formed were removed by filtration. The mother liquor was concentrated, and the residue thus obtained was dissolved by adding chloroform, the chloroform solution was washed with water and an aqueous solution saturated with sodium chloride. The chloroform solution was dried with anhydrous sodium sulfate, then the solvent was removed by evaporation. To the residue thus obtained was added 20 ml of ethanol, and converted into hydrochloride with 1.3 ml of concentrated hydrochloric acid. Recrystallized from ethanol-water to obtain 340 mg of 6-(4-geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.hydrochloride. monohydrate. Colorless needle-like crystals. Melting point: 265°-266° C. (dec.).

Workup

  1. customthe solvent was removed from the reaction mixture by evaporation
  2. customto the residue thus obtained
  3. customthe crystals formed
  4. customwere removed by filtration
  5. concentrationThe mother liquor was concentrated
  6. customthe residue thus obtained
  7. dissolutionwas dissolved
  8. washthe chloroform solution was washed with water
  9. dry with materialThe chloroform solution was dried with anhydrous sodium sulfate
  10. customthe solvent was removed by evaporation
  11. customTo the residue thus obtained
  12. customRecrystallized from ethanol-water

Sources & evidence

ORD record
ord-3cdefc7e369a4713b6b9a2bf2df4c8bd
Source dataset
uspto-grants-1989_07
Patent number
US04845100

Reaction notes

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