N6-Methyladenine → N6-methyl-9-[3-(4-phenyl-piperazino)-propyl]-adenine

HRID 1973236Notes

Reaction equation

HRID 1973236 reaction equation
[Na].[CH3:2][NH:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[NH:6][CH:7]=[N:8]2.[C:13]1([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27]Cl)[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(C)C>[CH3:2][NH:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:27][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 67955N6-MethyladenineHCID 139197Piperazine, 1-(3-chloropropyl)-4-phenyl-HCID 5360545Sodium

Product 1

HCID 86734243N6-methyl-9-[3-(4-phenyl-piperazino)-propyl]-adenineYield 45.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

1.38 g (0.06 mole) of sodium are dissolved in 120 ml of isopropanol. 8.9 g (0.06 mole) of N6 -methyl-adenine are added to this solution, which is then heated under reflux for 10 minutes, cooled and 15.8 g (0.066 mole) of 3-(4-phenyl-piperazino)-propyl chloride in 30 ml of isopropanol are added thereto. This reaction mixture is heated under reflux for 6 hours. Thereafter, it is cooled, suction filtered and sodium chloride washed out from the residue with water. After washing with water and drying, the product is recrystallized from isopropanol. There are obtained 9.5 g (45% of theory) of N6 -methyl-9-[3-(4-phenyl-piperazino)-propyl]-adenine, which has a melting point of 162°-163° C.

Workup

  1. temperatureis then heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturecooled
  4. temperatureThis reaction mixture is heated
  5. temperatureunder reflux for 6 hours
  6. temperatureThereafter, it is cooled
  7. filtrationsuction filtered
  8. washsodium chloride washed out from the residue with water
  9. washAfter washing with water
  10. customdrying
  11. customthe product is recrystallized from isopropanol

Sources & evidence

ORD record
ord-0bc1cf3c13ec47ff995bf95cc035ab77
Source dataset
uspto-grants-1976_12
Patent number
US03996361

Reaction notes

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