1-Propanol → 1H-Purin-6-amine, N-dodecyl-

HRID 1995738Notes

Reaction equation

HRID 1995738 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[CH2:11]([NH2:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(O)CC>O>[CH2:11]([NH:23][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 13583DodecylamineHCID 53592776-Chloropurine

Product 1

HCID 1014291H-Purin-6-amine, N-dodecyl-Yield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloropurine (2.5 g, 0.016 mole) and n-dodecylamine (7.4 g, 0.04 mole) in 40 ml. of n-propanol was refluxed for 5 hours. The reaction mixture was stirred at room temperature for 1 hour and cooled with water (15° C.) for another hour. The product was collected by filtration, washed by two 5 ml. portions of n-propanol and dried in a vacuum oven overnight to give 4.5 g (92% yield) of 6-n-dodecylaminopurine, a colorless solid, m.p. 159°-160° C., λ max (H2O)=268 nm, ε=17.3×103.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed by two 5 ml
  3. dry with materialportions of n-propanol and dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-99f6806577a04b14a46fb9c7eb21f483
Source dataset
uspto-grants-1983_09
Patent number
US04405781

Reaction notes

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