Piperazine → 1-(2-Pyrimidinyl)piperazine

HRID 979489Notes

Reaction equation

HRID 979489 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1>O>[N:15]1[CH:16]=[CH:17][CH:18]=[N:19][C:14]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 10340Sodium CarbonateHCID 744042-Chloropyrimidine

Product 1

HCID 887471-(2-Pyrimidinyl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred, warm (approximately 50°) solution of anhydrous piperazine (100 g, 1.16 mole) and sodium carbonate (58 g, 0.47 mole) in 465 mL water was added 2-chloropyrimidine (53 g, 0.46 mole) in portions over about 1 hour. External cooling was required to maintain the temperature in the 50°-65° range. After the addition, the stirred reaction mixture was kept in the temperature range of 50°-65° for one hour and then allowed to slowly cool to 35° over a 2 hour period. The mixture was filtered, removing 1,4-dipyrimidinylpiperazine, and the filtrate was extracted with 350 mL portions of chloroform. The chloroform extracts were dried (MgSO4) and concentrated to 62 g (82%) of an oily solid which can be purified by distillation (b.p. 118°-120°/2 Torr.) or converted to a salt form.

Workup

  1. temperatureExternal cooling
  2. temperatureto maintain the temperature in the 50°-65° range
  3. additionAfter the addition
  4. customthe stirred reaction mixture
  5. temperatureto slowly cool to 35° over a 2 hour period
  6. filtrationThe mixture was filtered
  7. customremoving 1,4-dipyrimidinylpiperazine
  8. extractionthe filtrate was extracted with 350 mL portions of chloroform
  9. dry with materialThe chloroform extracts were dried (MgSO4)
  10. concentrationconcentrated to 62 g (82%) of an oily solid which
  11. distillationcan be purified by distillation (b.p. 118°-120°/2 Torr.)

Sources & evidence

ORD record
ord-9bd76a1193a34e35a0cb5a034c2b1da1
Source dataset
uspto-grants-1987_05
Patent number
US04668687

Reaction notes

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