Piperazine → HCID 22414344, compound

HRID 1721290Notes

Reaction equation

HRID 1721290 reaction equation
Cl[C:2]1([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[NH:3]1.[NH:18]1[CH2:23][CH2:22]N[CH2:20][CH2:19]1.C([N:26]1CCOCC1)C>>[N:13]1([C:2]2[N:7]=[C:6]([N:18]3[CH2:23][CH2:22][CH2:20][CH2:19]3)[CH:5]=[C:4]([N:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)[N:3]=2)[CH2:17][CH2:16][NH:26][CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 7525EthylmorpholineHCID 22414359HCID 22414359, compound

Product 1

HCID 22414344HCID 22414344, compound

Procedure

A mixture of 10.0 g (34.7 mmoles) of 2-chloro-2,6-bis(pyrrolidino)pyrimidine, 11.95 g (138.8 mmoles) of piperazine and 150 ml of N-ethylmorpholine is boiled under reflux under nitrogen for 25 hours, then the solvent and excess piperazine are distilled off under environmental pressure. After adding 100 ml of water to the residue, water is 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 evaporation residue is purified by chromatography on a silica gel column. By using a 9:1 mixture of chloroform and methanol as eluent and recrystallizing the product from hexane, the title compound is obtained in a yield of 8.54 g (81.4%), m.p.: 152°-160° C.

Workup

  1. temperatureunder reflux under nitrogen for 25 hours
  2. distillationthe solvent and excess piperazine are distilled off under environmental pressure
  3. additionAfter adding 100 ml of water to the residue, water
  4. distillationis distilled off until the head temperature
  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 evaporation residue is purified by chromatography on a silica gel column
  12. additiona 9:1 mixture of chloroform and methanol as eluent
  13. customrecrystallizing the product from hexane

Sources & evidence

ORD record
ord-f043f7e5762a433684c405945ef87007
Source dataset
uspto-grants-1996_04
Patent number
US05510345

Reaction notes

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