Morpholine → 4-(2-chloro-9H-purin-6-yl)morpholine

HRID 1876489Notes

Reaction equation

HRID 1876489 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10](Cl)[N:9]=1>C(O)C>[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][NH:14]2)=[C:10]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 53244122,6-Dichloropurine

Product 1

HCID 32746034-(2-chloro-9H-purin-6-yl)morpholineYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Morpholine (46.9 ml, 538.2 mmol) was added to an ethanol solution (1.2 l) of 2,6-dichloropurine (50.9 g, 269.1 mmol) at room temperature and the resulting mixture was stirred and heated to reflux for 2.5 hours. The reaction mixture was left standing to cool and then concentrated until the solvent was reduced nearly by half in volume and the solid was collected by filtration. The solid was washed with ethanol and dried at 50° C. under reduced pressure to give a mixture (63.3 g, 95%) of the title compound and morpholine hydrochloride (approx. 13:1) as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. concentrationconcentrated until the solvent
  6. filtrationthe solid was collected by filtration
  7. washThe solid was washed with ethanol
  8. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-6ae7aa92ce584d2c851303b1b195ace1
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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