Piperazine → HCID 9818025, compound

HRID 1078938Notes

Reaction equation

HRID 1078938 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[N:5]=[C:4]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])[N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(N1CCOCC1)C>[CH3:15][C:14]([NH:13][C:4]1[N:5]=[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:7]=[C:2]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[N:3]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 19428515HCID 19428515, compound

Product 1

HCID 9818025HCID 9818025, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7525EthylmorpholineSolvent

Procedure

A mixture containing 9.58 g (34.7 mmoles) of 4-chloro-2,6-bis(1,1-dimethylethylamino)pyrimidine, 11.95 g (138.8 mmoles) of piperazine and 150 ml of N-ethylmorpholine is boiled under reflux and nitrogen atmosphere for 25 hours, then the solvent and the excess of piperazine are distilled off under atmospheric pressure. Subsequently, 100 ml of water are added to the residue and the distillation is continued until the head temperature reaches 100° C. After cooling down, the residue is distributed between 200 ml of chloroform and 30 ml of 10% sodium hydroxide solution. After separation the organic phase is washed 4 times with 50 ml of water each, then dried and evaporated. The residue is purified by chromatography on a silica gel column by using a 9:1 mixture of chloroform/methanol as eluent. After evaporating the eluate the residue is recrystallized from hexane to obtain the title compound in a yield of 64%, m.p.: 142°-145° C.

Workup

  1. temperatureunder reflux
  2. distillationthe solvent and the excess of piperazine are distilled off under atmospheric pressure
  3. additionSubsequently, 100 ml of water are added to the residue
  4. distillationthe distillation
  5. customreaches 100° C
  6. temperatureAfter cooling down
  7. customAfter separation the organic phase
  8. washis washed 4 times with 50 ml of water each,
  9. customthen dried
  10. customevaporated
  11. customThe residue is purified by chromatography on a silica gel column
  12. additiona 9:1 mixture of chloroform/methanol as eluent
  13. customAfter evaporating the eluate the residue
  14. customis recrystallized from hexane

Sources & evidence

ORD record
ord-db36227645724a218934378b29065128
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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