Hydrochloric Acid → 7-{3-[4-(3,4,5-Trimethoxyphenyl)-piperazinyl]propoxy}-3,4-dihydrocarbostyril dihydrochloride

HRID 621559

Reaction equation

HRID 621559 reaction equation
[Cl:1]CCCO[CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26].[C:35](=[O:38])([O-])O.[Na+].[ClH:40].[CH2:41](O)[CH3:42]>CS(C)=O.N1C=CC=CC=1>[ClH:1].[ClH:40].[CH3:28][O:27][C:23]1[CH:22]=[C:21]([N:29]2[CH2:34][CH2:33][N:32]([CH2:41][CH2:42][CH2:35][O:38][C:11]3[CH:10]=[C:9]4[C:14]([CH2:15][CH2:6][C:7](=[O:16])[NH:8]4)=[CH:13][CH:12]=3)[CH2:31][CH2:30]2)[CH:20]=[C:19]([O:18][CH3:17])[C:24]=1[O:25][CH3:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 516892Sodium BicarbonateHCID 38387651-(3,4,5-Trimethoxyphenyl)piperazineHCID 1317159243-Chloropropoxy-3,4-dihydrocarbostyril

Product 1

HCID 128995267-{3-[4-(3,4,5-Trimethoxyphenyl)-piperazinyl]propoxy}-3,4-dihydrocarbostyril dihydrochlorideYield 61%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

12.4 grams of 7-(3-chloropropoxy-3,4-dihydrocarbostyril, 1 g of pyridine and 2.6 g of 4-(3,4,5-trimethoxyphenyl)piperazine are mixed in 20 ml of dimethylsulfoxide, then stirred at 80°-90° C. for 5 hours. The reaction mixture is poured into 80 ml of 2% aqueous solution of sodium hydrogencarbonate and the organic layer is extracted with chloroform. The chloroform layer is washed with water, dried and chloroform is removed by distillation. The residue thus obtained is dissolved in 30 ml of ethanol and dried hydrogen chloride gas is blown into the ethanol solution. The crystals thus precipitated are collected by filtration and recrystallized from methanol-ethanol to obtain 3.2 g (yield: 61%) of 7-{3-[4-(3,4,5-trimethoxyphenyl)-piperazinyl]propoxy}-3,4-dihydrocarbostyril dihydrochloride in the form of colorless needle-like crystals with a melting point of 225°-227° C.

Workup

  1. extractionthe organic layer is extracted with chloroform
  2. washThe chloroform layer is washed with water
  3. customdried
  4. customchloroform is removed by distillation
  5. customThe residue thus obtained
  6. customThe crystals thus precipitated
  7. filtrationare collected by filtration
  8. customrecrystallized from methanol-ethanol

Sources & evidence

ORD record
ord-6c25e9bb8ead4005a472cd4def0bbcbc
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Linked notes

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