Diethyl chlorophosphate → 5-(4-Geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.hydrochloride

HRID 231106Notes

Reaction equation

HRID 231106 reaction equation
C([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)(O)=O.P([Cl:23])(OCC)([O:17][CH2:18]C)=O.[CH2:24]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)/[CH:25]=[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])\[CH3:27].C(=O)(O)[O-].[Na+]>O1CCCC1.C(N(CC)CC)C>[ClH:23].[CH2:24]([N:34]1[CH2:35][CH2:36][N:37]([C:18]([C:5]2[CH:4]=[CH:13][CH:12]=[C:11]3[C:6]=2[CH2:7][CH2:8][C:9](=[O:14])[NH:10]3)=[O:17])[CH2:38][CH2:39]1)/[CH:25]=[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:32])[CH3:33])\[CH3:27]

Participants

7

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 516892Sodium BicarbonateHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acidHCID 14497703Geranylpiperazine

Product 1

HCID 1317159935-(4-Geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.hydrochloride

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

1.6 Grams of 6-carboxy-3,4-dihydrocarbostyril and 0.8 ml of triethylamine were suspended in 10 ml of THF (tetrahydrofuran), to this suspension was added dropwise 10 ml of THF solution containing 1.0 g of diethyl chlorophosphate at room temperature under stirring, then the whole mixture was stirred at room temperature for 3 hours. Then to this reaction mixture was added dropwise 10 ml of THF solution containing 1.4 g of geranylpiperazine, then the whole reaction mixture was stirred further at room temperature for 10 hours. After the reaction was finished, the crystals formed in the reaction mixture were removed by filtration, then the mother liquor was concentrated. To the residue thus obtained was added an aqueous solution saturated with sodium bicarbonate, then extracted with chloroform. The organic layer was washed with water and an aqueous solution saturated with sodium chloride, and dried with anhydrous sodium sulfate, then the solvent was removed by evaporation. The residue was converted into hydrochloride by adding ethanol-concentrated hydrochloric acid. Recrystallized from ethanol-water to obtain 1.08 g of 5-(4-geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril.hydrochloride.monohydrate. Colorless needle-like crystals. Melting point: 265°-266° C. (dec.).

Workup

  1. stirringthe whole mixture was stirred at room temperature for 3 hours
  2. customthe whole reaction mixture
  3. stirringwas stirred further at room temperature for 10 hours
  4. customthe crystals formed in the reaction mixture
  5. customwere removed by filtration
  6. concentrationthe mother liquor was concentrated
  7. customTo the residue thus obtained
  8. extractionextracted with chloroform
  9. washThe organic layer was washed with water
  10. dry with materialan aqueous solution saturated with sodium chloride, and dried with anhydrous sodium sulfate
  11. customthe solvent was removed by evaporation
  12. additionby adding ethanol-concentrated hydrochloric acid
  13. customRecrystallized from ethanol-water

Sources & evidence

ORD record
ord-524a25d788d34d4eb6b7ea7f59c37370
Source dataset
uspto-grants-1989_07
Patent number
US04845100

Reaction notes

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