Isobutyl chloroformate → 6-(4-Geranyl-1-piperazinylcarbonyl)carbostyril hydrochloride monohydrate

HRID 231107Notes

Reaction equation

HRID 231107 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])[CH:8]=[CH:7]2)([OH:3])=[O:2].[Cl:15]C(OCC(C)C)=O.[CH2:23]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)/[CH:24]=[C:25](/[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])\[CH3:26].C(=O)(O)[O-].[Na+]>CS(C)=O.C(N(CC)CC)C>[OH2:2].[ClH:15].[CH2:23]([N:33]1[CH2:34][CH2:35][N:36]([C:1]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH:8]=[CH:7]3)=[O:3])[CH2:37][CH2:38]1)/[CH:24]=[C:25](/[CH2:27][CH2:28][CH:29]=[C:30]([CH3:31])[CH3:32])\[CH3:26]

Participants

7

Reactant 4

HCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 133421682-Oxo-1,2-dihydroquinoline-6-carboxylic acidHCID 14497703Geranylpiperazine

Product 1

HCID 200345316-(4-Geranyl-1-piperazinylcarbonyl)carbostyril hydrochloride monohydrate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 8471TriethylamineSolvent

Procedure

34.5 Grams of 6-carboxycarbostyril and 31 ml of triethylamine were dissolved in 350 ml of DMF (dimethyl sulfoxide), and to this solution was added dropwise a solution containing 28 ml of isobutyl chloroformate and 14 ml of DMF at room temperature under stirring. After stirred at room for 1 hour, 21 ml of DMF solution containing 46.7 g of geranylpiperazine was added dropwise thereto, and the whole mixture was stirred at room temperature for 10 hours. The reaction mixture was poured in an aqueous solution saturated with sodium bicarbonate, then extracted with chloroform. The chloroform layer was washed with water, an aqueous solution saturated with sodium chloride in this order, then dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, the residue thus obtained was crystallized by adding diethyl ether, and the crystals were collected by filtration. The crystals were dissolved in ethanol and was converted into hydrochloride by adding concentrated hydrochloric acid. The crude crystals obtained were recrystallized from ethanol-water to obtain 32 g of 6-(4-geranyl-1-piperazinylcarbonyl)carbostyril hydrochloride monohydrate. Colorless needle-like crystals. Melting point: 265°-266° C. (dec.).

Workup

  1. additionto this solution was added dropwise a solution
  2. stirringAfter stirred at room for 1 hour
  3. additionwas added dropwise
  4. stirringthe whole mixture was stirred at room temperature for 10 hours
  5. extractionextracted with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialan aqueous solution saturated with sodium chloride in this order, then dried with anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customthe residue thus obtained
  10. customwas crystallized
  11. additionby adding diethyl ether
  12. filtrationthe crystals were collected by filtration
  13. dissolutionThe crystals were dissolved in ethanol
  14. additionby adding concentrated hydrochloric acid
  15. customThe crude crystals obtained
  16. customwere recrystallized from ethanol-water

Sources & evidence

ORD record
ord-fa829fc20dc34fee946c6228ba984fba
Source dataset
uspto-grants-1989_07
Patent number
US04845100

Reaction notes

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