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

HRID 2083720Notes

Reaction equation

HRID 2083720 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 2N 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 2N 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-0978481439f54e65b05333b84fd73057
Source dataset
uspto-grants-1978_04
Patent number
US04086347

Reaction notes

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