Reaction #56066

Reaction equation

sodium methylate

sodium

5-(1-hydroxy-2-tert-butylaminopropyl)-8-hydroxycarbostyril hydrochloride

→

8-(3,4-methylenedioxyphenylcarbonyloxy)-5-(1-hydroxy-2-tert-butylaminopropyl)carbostyril

Solvents

methanol

methanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added to the suspension
2. 2
   ConcentrationThe mixture was then concentrated to dryness
3. 3
   workup.DISSOLUTIONthe resulting residue was dissolved in 10 ml of dimethylformamide
4. 4
   workup.DISSOLUTION593 mg of piperonylyl chloride dissolved in 5 ml of dimethylformamide
5. 5
   workup.ADDITIONwas then added dropwise to the mixture
6. 6
   Temperaturewhile cooling with ice-water
7. 7
   workup.ADDITIONwater was added to the mixture
8. 8
   Extractionfollowed by extraction with chloroform
9. 9
   OtherChloroform was removed by distillation, and diethyl ether
10. 10
    workup.ADDITIONwas added to the residue
11. 11
    Otherto crystallize the product
12. 12
    OtherThe crystals thus obtained
13. 13
    Otherwere separated by filtration
14. 14
    Washwashed with diethyl ether
15. 15
    Otherrecrystallized from a mixture of chloroform and diethyl ether

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.

Source