N-butyl-7H-purin-6-amine → HCID 20357456, compound

HRID 2083721Notes

Reaction equation

HRID 2083721 reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[NH:8][CH:9]=[N:10]2)[CH2:2][CH2:3][CH3:4].[Na].[F:16][C:17]1[CH:34]=[CH:33][C:20]([O:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][Cl:32])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1>C(O)(C)C>[ClH:32].[ClH:32].[CH2:1]([NH:5][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:31][CH2:30][CH2:29][N:26]1[CH2:27][CH2:28][CH:23]([CH2:22][O:21][C:20]2[CH:33]=[CH:34][C:17]([F:16])=[CH:18][CH:19]=2)[CH2:24][CH2:25]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 521516N-butyl-7H-purin-6-amineHCID 5360545SodiumHCID 20357455HCID 20357455, compound

Product 1

HCID 20357456HCID 20357456, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

9.55 g (0.05 mole) of N6 -n-butyladenine are added to a solution of 1.15 g (0.05 mole) of sodium in 200 ml of isopropanol and the reaction mixture is heated under reflux for 10 minutes. After cooling, 22.8 g (0.08 mole) of 3-[4-(4-fluorophenoxymethyl)-piperidino]-propyl chloride in 50 ml of isopropanol are added thereto. After boiling under reflux for 6 hours, the reaction mixture is evaporated in a vacuum and the residue is taken up in methylene chloride, washed with 2N aqueous sodium hydroxide solution and subsequently with water, dried over anhydrous sodium sulfate, evaporated and the residue is taken up in acetone and mixed with excess saturated ethereal hydrogen chloride solution. The salt which precipitates out is filtered off and recrystallized from isopropanol. There are obtained 14.6 g (57% of theory) of N6 -n-butyl-9-{3-[4-(4-fluorophenoxymethyl)-piperidino]-propyl}-adenine dihydrochloride; m.p. 180° - 182° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 10 minutes
  3. temperatureAfter cooling
  4. temperatureunder reflux for 6 hours
  5. customthe reaction mixture is evaporated in a vacuum
  6. washwashed with 2N aqueous sodium hydroxide solution and subsequently with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. additionmixed with excess saturated ethereal hydrogen chloride solution
  10. customThe salt which precipitates out
  11. filtrationis filtered off
  12. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-1e71ab4ee7f243dea04a4972815eff6b
Source dataset
uspto-grants-1978_04
Patent number
US04086347

Reaction notes

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