Water → HCID 18958823, compound

HRID 1708371Notes

Reaction equation

HRID 1708371 reaction equation
[ClH:1].[N:2]1([C:7]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:17](=[O:27])[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:26])[CH2:12][CH2:11]2)=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(Cl)[Cl:36]>O1CCCC1>[ClH:36].[ClH:1].[N:2]1([CH2:7][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:17](=[O:27])[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:26])[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 18958787HCID 18958787, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18958823HCID 18958823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.0 Grams of 3-[4-(1-pyrrolidinylcarbonylmethyl)-1-piperazinyl]-8-methylcarbostyril hydrochloride was suspended in 20 ml of tetrahydrofuran, to this suspension was added dropwise a solution of 0.32 g of lithium aluminium hydride in 20 ml of tetrahydrofuran under nitrogen gas stream with stirring. This reaction mixture was stirred at the same temperature for 30 minutes, then the reaction mixture was refluxed by heating on a oil bath for 2 hours. To the reaction mixture was added water and methylene chloride and filtered with Celite (a trademark for diatomaceous earth product, manufactured by Johns Manville Sales Corp., U.S.A.). The filtrate was extracted with methylene chloride, washed with an aqueous solution saturated with sodium chloride, and dried with anhydrous sodium sulfate, then concentrated by removing the solvent under reduced pressure, the residue thus obtained was purified by a silica gel column chromatography (eluent: methylene chloride:methanol=10:1). The desired product was converted into dihydrochloride by using ethanol-HCl, then recrystallized from ethanol-water to obtain 1.15 g of 3-{4-[2-(1-pyrrolidinyl)ethyl]-1 -piperazinyl}-8-methylcarbostyril dihydrochloride. Light yellow needle-like crystals. Melting point: over 300° C.

Workup

  1. stirringThis reaction mixture was stirred at the same temperature for 30 minutes
  2. temperaturethe reaction mixture was refluxed
  3. temperatureby heating on a oil bath for 2 hours
  4. filtrationfiltered with Celite (a trademark for diatomaceous earth product
  5. extractionThe filtrate was extracted with methylene chloride
  6. washwashed with an aqueous solution saturated with sodium chloride
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customby removing the solvent under reduced pressure
  10. customthe residue thus obtained
  11. customwas purified by a silica gel column chromatography (eluent: methylene chloride:methanol=10:1)
  12. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-92ea0664f0c34c65af5745422023fb83
Source dataset
uspto-grants-1994_10
Patent number
US05358949

Reaction notes

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