Adenine → 9-[3-(4-Phenoxymethylpiperidino)-propyl]-adenine

HRID 1389244Notes

Reaction equation

HRID 1389244 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[Na].[O:12]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28]Cl)[CH2:22][CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(C)C>[O:12]([CH2:19][CH:20]1[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][N:5]2[CH:6]=[N:7][C:8]3[C:4]2=[N:3][CH:2]=[N:1][C:9]=3[NH2:10])[CH2:24][CH2:25]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 5360545SodiumHCID 20570886HCID 20570886, compound

Product 1

HCID 202988729-[3-(4-Phenoxymethylpiperidino)-propyl]-adenineYield 64%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

9.45 g (0.07 mole) of adenine are added to a solution of 1.6 g (0.07 mole) of sodium in 250 ml of isopropanol and the reaction mixture heated under reflux for 10 minutes. It is then cooled and 21.4 g (0.08 mole) of 3-(4-phenoxymethylpiperidino)-propyl chloride in 50 ml of isopropanol added thereto. After stirring the reaction mixture under reflux for 6 hours, it is evaporated in a vacuum, the residue is taken up in methylene chloride, the methylene chloride solution is washed with 2 N aqueous sodium hydroxide solution and subsequently with water, dried over anhydrous sodium sulfate, evaporated and the residue recrystallized from isopropanol. There are obtained 16.4 g (64% of theory) of 9-[3-(4-phenoxymethylpiperidino)-propyl]-adenine; m.p. 142°-144° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 10 minutes
  3. temperatureIt is then cooled
  4. temperatureunder reflux for 6 hours
  5. customit is evaporated in a vacuum
  6. washthe methylene chloride solution is washed with 2 N aqueous sodium hydroxide solution and subsequently with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customthe residue recrystallized from isopropanol

Sources & evidence

ORD record
ord-4eadf0fdb33b4955bfbc036c50e4a3d9
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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