Hydrochloric Acid → 6-{1-Oxo-4-[4-(3,4-methylenedioxy-phenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril monohydrochloride

HRID 1285433Notes

Reaction equation

HRID 1285433 reaction equation
[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)[CH2:3][CH2:4][CH2:5][Cl:6].[I-].[Na+].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:23][C:22]=2[O:21]1.C1CCN2C(=NCCC2)CC1.C(=O)([O-])O.[Na+].Cl>CS(C)=O.CO>[ClH:6].[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)[CH2:3][CH2:4][CH2:5][N:32]1[CH2:33][CH2:34][N:29]([C:24]2[CH:25]=[CH:26][C:27]3[O:28][CH2:20][O:21][C:22]=3[CH:23]=2)[CH2:30][CH2:31]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 47420031-(1,3-Benzodioxol-5-yl)piperazineHCID 128335166-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

Product 1

HCID 130648366-{1-Oxo-4-[4-(3,4-methylenedioxy-phenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril monohydrochloride

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2.7 Grams of 6-(1-oxo-4-chlorobutyl)-3,4-dihydrocarbostyril and 1.5 g of sodium iodide were mixed in 30 ml of dimethyl sulfoxide and the mixture was stirred at 50° C. for 2 hours. Then to the reaction mixture were added 2.0 g of 4-(3,4-methylenedioxyphenyl)piperazine and 3 g of DBU and the reaction mixture was stirred at 70°-80° C. for 5 hours. After the reaction was completed, the reaction mixture was poured into 10 ml of 2%-sodium hydrogencarbonate and the organic layer was extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation. To the residue thus obtained were added 50 ml of methanol and 5 ml of concentrated hydrochloric acid and the mixture was concentrated under a reduced pressure to dryness. The residue thus obtained was crystallized by adding ethanol-acetone to obtain crude crystals, and the crude crystals were recrystallized from ethanol-water. 2.1 Grams of 6-{1-oxo-4-[4-(3,4-methylenedioxy-phenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril monohydrochloride in colorless powdery crystals were obtained.

Workup

  1. stirringthe reaction mixture was stirred at 70°-80° C. for 5 hours
  2. extractionthe organic layer was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. customchloroform was removed by distillation
  6. customTo the residue thus obtained
  7. concentrationthe mixture was concentrated under a reduced pressure to dryness
  8. customThe residue thus obtained
  9. customwas crystallized
  10. additionby adding ethanol-acetone
  11. customto obtain crude crystals
  12. customthe crude crystals were recrystallized from ethanol-water

Sources & evidence

ORD record
ord-31ac924065894dfe8c95c79b38c8169d
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

Loading…