Propylamine → N6-n-propyl-9-[3-(4-phenoxymethylpiperidino)-propyl]-adenine

HRID 2083723Notes

Reaction equation

HRID 2083723 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].Cl[C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:19]1>C(O)CC>[CH2:1]([NH:4][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([CH2:24][O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:22][CH2:23]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 20357451HCID 20357451, compound

Product 1

HCID 20357448N6-n-propyl-9-[3-(4-phenoxymethylpiperidino)-propyl]-adenineYield 74%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

50 ml of n-propylamine are added to a solution of 11.6 g (0.03 mole) of 6-chloro-9-[3-(4-phenoxymethylpiperidino)-propyl]-purine in 100 ml of n-propanol and the reaction mixture is heated under reflux for 6 hours. It is then evaporated in a vacuum and the residue extracted with diethyl ether. After evaporation of the solvent and recrystallization of the residue from cyclohexane, there are obtained 9.1 g of N6 -n-propyl-9-[3-(4-phenoxymethylpiperidino)-propyl]-adenine (74% of theory); m.p. 62° - 63° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 6 hours
  3. customIt is then evaporated in a vacuum
  4. extractionthe residue extracted with diethyl ether
  5. customAfter evaporation of the solvent and recrystallization of the residue from cyclohexane, there

Sources & evidence

ORD record
ord-fc21503edae344a0a419aa5322826fff
Source dataset
uspto-grants-1978_04
Patent number
US04086347

Reaction notes

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