Hydrochloric Acid → HCID 12899573, compound

HRID 569961Notes

Reaction equation

HRID 569961 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:17])[CH:3]=1.[I-].[Na+].C(=O)([O-])O.[Na+].[ClH:25].[CH3:26][N:27]([CH3:30])[CH:28]=O>CO.CC(C)=O>[ClH:16].[ClH:25].[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][N:5]3[CH2:6][CH2:28][N:27]([C:30]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:26][CH2:4]3)=[CH:9][CH:10]=2)[NH:5][C:4](=[O:17])[CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 12899555HCID 12899555, compound

Product 1

HCID 12899573HCID 12899573, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

2.7 Grams of 4-methyl-7-(3-chloropropoxy)carbostyril and 1.8 g of sodium iodide are mixed with 50 ml of acetone and heated for 3 hours under refluxing conditions. Then 50 ml of dimethylformamide is added thereto and acetone is removed by distillation under reduced pressure. Next, 1.5 g of triethylamine and 1.8 g of 4-phenylpiperazine are added thereto and stirred for 3 hours at 80°-90° C. and dimethylformamide is removed by distillation under reduced pressure. To the residue thus obtained is added 5% sodium hydrogencarbonate aqueous solution to effect crystallization of the product and the precipitates formed are collected by filtration, washed with water, washed with isopropanol, further washed with ether and dried. The crude crystals thus obtained are dispersed in 80 ml of methanol, and dissolved by adding 5 ml of concentrated hydrochloric acid, then concentrated under a reduced pressure to dryness. The thus obtained residue is recrystallized from methanol-ether to obtain 3.6 g (yield: 80%) of 4-methyl-7-[3-(4-phenylpiperazinyl)propoxy]carbostyril dihydrochloride in the form of colorless crystals with a melting point of 253°-254° C. (decomp.).

Workup

  1. temperatureheated for 3 hours under refluxing conditions
  2. customacetone is removed by distillation under reduced pressure
  3. additionNext, 1.5 g of triethylamine and 1.8 g of 4-phenylpiperazine are added
  4. customdimethylformamide is removed by distillation under reduced pressure
  5. customTo the residue thus obtained
  6. customcrystallization of the product
  7. customthe precipitates formed
  8. filtrationare collected by filtration
  9. washwashed with water
  10. washwashed with isopropanol
  11. washfurther washed with ether
  12. customdried
  13. customThe crude crystals thus obtained
  14. dissolutiondissolved
  15. concentrationconcentrated under a reduced pressure to dryness
  16. customThe thus obtained residue is recrystallized from methanol-ether

Sources & evidence

ORD record
ord-8f6bfdd8a5f341fcbb06b862932652c7
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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