Toluene → HCID 12899429, compound

HRID 621558Notes

Reaction equation

HRID 621558 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[NH:11]2.[CH:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:21][CH:22]=1.C1(C)C=CC=CC=1.CCCCCC>C(Cl)(Cl)Cl>[ClH:1].[C:20]1([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:15]=[CH:14][CH:13]=[C:12]4[C:7]=3[CH2:8][CH2:9][C:10](=[O:16])[NH:11]4)[CH2:25][CH2:24]2)[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 70961-PhenylpiperazineHCID 8058HexaneHCID 12899139HCID 12899139, compound

Product 1

HCID 12899429HCID 12899429, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.8 grams of 5-(3-chloropropoxy)-3,4-dihydrocarbostyril and 4 g of phenylpiperazine are mixed with 40 ml of toluene and heated for 24 hours under refluxing conditions. Then the reaction mixture is concentrated under reduced pressure to dryness. The residue thus obtained is dissolved in 80 ml of chloroform and the chloroform layer is washed twice with 5.0% of sodium hydrogencarbonate aqueous solution, further washed twice with water, dried with anhydrous sodium sulfate and chloroform is removed by distillation. To the residue thus obtained is added hexane and the insoluble material is collected by filtration, then the insoluble material is dissolved in 30 ml of 5% HCl-methanol solution and concentrated under reduced pressure to dryness. Then the residue thus obtained is recrystallized from methanol-ether to obtain 3.2 of 5-[3-(4-phenylpiperazinyl)propoxy]-3,4-dihydrocarbostyril monohydrochloride in the form of colorless crystals with a melting point of 262° C. (decomposition).

Workup

  1. temperatureheated for 24 hours under refluxing conditions
  2. concentrationThen the reaction mixture is concentrated under reduced pressure to dryness
  3. customThe residue thus obtained
  4. washthe chloroform layer is washed twice with 5.0% of sodium hydrogencarbonate aqueous solution
  5. washfurther washed twice with water
  6. dry with materialdried with anhydrous sodium sulfate and chloroform
  7. customis removed by distillation
  8. customTo the residue thus obtained
  9. filtrationthe insoluble material is collected by filtration
  10. dissolutionthe insoluble material is dissolved in 30 ml of 5% HCl-methanol solution
  11. concentrationconcentrated under reduced pressure to dryness
  12. customThen the residue thus obtained
  13. customis recrystallized from methanol-ether

Sources & evidence

ORD record
ord-d7baae6a06c94672a97ff799bb6abdb8
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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