Piperazine → HCID 9818025, compound

HRID 1078281Notes

Reaction equation

HRID 1078281 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, compound

Reagents, catalysts & solvents 1

HCID 7525EthylmorpholineSolvent

Procedure

A mixture containing 10.0 g (38.9 mmoles) of 4-chloro-2,6-bis(1,1-dimethylethylamino)pyrimidine, 13.42 g (155.8 mmoles) of piperazine and 150 ml of N-ethylmorpholine is boiled under reflux under nitrogen for 25 hours, then the solvent and piperazine are distilled off under atmospheric pressure. Water is added to the residue and distilled off 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 and methanol. After recrystallizing the eluted product from hexane, the title compound is obtained in a yield of 7.65 g (64%), m.p.:142°-145° C.

Workup

  1. temperatureunder reflux under nitrogen for 25 hours
  2. distillationthe solvent and piperazine are distilled off under atmospheric pressure
  3. additionWater is added to the residue
  4. distillationdistilled off until the head temperature
  5. customreaches 100° C
  6. temperatureAfter cooling down the residue
  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 and methanol
  13. customAfter recrystallizing the eluted product from hexane

Sources & evidence

ORD record
ord-55be2e54d6094cf78da0f7344f66e454
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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