Sodium → 8-(3,4-Methylenedioxyphenylcarbonyloxy)-5-(1-hydroxy-2-tert-butylaminopropyl)carbostyril

HRID 27788Notes

Reaction equation

HRID 27788 reaction equation
Cl.[OH:2][CH:3]([C:11]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15](=[O:22])[NH:16]2)[CH:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:5].[CH3:23][O-:24].[Na+].[Na]>CO>[CH2:23]1[O:21][C:18]2[CH:19]=[CH:20][C:11]([C:3]([O:21][C:18]3[CH:19]=[CH:20][C:11]([CH:3]([OH:2])[CH:4]([NH:6][C:7]([CH3:10])([CH3:8])[CH3:9])[CH3:5])=[C:12]4[C:17]=3[NH:16][C:15](=[O:22])[CH:14]=[CH:13]4)=[O:2])=[CH:12][C:17]=2[O:24]1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 23342050HCID 23342050, compound

Product 1

HCID 233421028-(3,4-Methylenedioxyphenylcarbonyloxy)-5-(1-hydroxy-2-tert-butylaminopropyl)carbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1 g of 5-(1-hydroxy-2-tert-butylaminopropyl)-8-hydroxycarbostyril hydrochloride was suspended in 15 ml of methanol, and sodium methylate prepared from 155 mg of sodium metal and 3.3 ml of absolute methanol was added to the suspension. The mixture was then concentrated to dryness, and the resulting residue was dissolved in 10 ml of dimethylformamide. 593 mg of piperonylyl chloride dissolved in 5 ml of dimethylformamide was then added dropwise to the mixture while cooling with ice-water. The mixture was then stirred for 1 hour, and water was added to the mixture followed by extraction with chloroform. Chloroform was removed by distillation, and diethyl ether was added to the residue to crystallize the product. The crystals thus obtained were separated by filtration, washed with diethyl ether and recrystallized from a mixture of chloroform and diethyl ether to obtain 520 mg of 8-(3,4-methylenedioxyphenylcarbonyloxy)-5-(1-hydroxy-2-tert-butylaminopropyl)carbostyril having a melting point of 156°-157° C.

Workup

  1. additionwas added to the suspension
  2. concentrationThe mixture was then concentrated to dryness
  3. dissolutionthe resulting residue was dissolved in 10 ml of dimethylformamide
  4. dissolution593 mg of piperonylyl chloride dissolved in 5 ml of dimethylformamide
  5. additionwas then added dropwise to the mixture
  6. temperaturewhile cooling with ice-water
  7. additionwater was added to the mixture
  8. extractionfollowed by extraction with chloroform
  9. customChloroform was removed by distillation, and diethyl ether
  10. additionwas added to the residue
  11. customto crystallize the product
  12. customThe crystals thus obtained
  13. customwere separated by filtration
  14. washwashed with diethyl ether
  15. customrecrystallized from a mixture of chloroform and diethyl ether

Sources & evidence

ORD record
ord-6a63ee114ab542759a6f79ccfdf47334
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

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