Piperazine → HCID 21916439, compound

HRID 1246223Notes

Reaction equation

HRID 1246223 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]=[C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:11]=[CH:10][N:9]=1>C(O)C>[CH2:17]([N:14]([CH2:15][CH3:16])[C:12]1[CH:11]=[CH:10][N:9]=[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[N:13]=1)[CH3:18]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 126793942-chloro-4-(diethylamino)pyrimidine

Product 1

HCID 21916439HCID 21916439, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of piperazine (5.8 g, 67.33 mmol) and N-(2-chloro-4-pyrimidinyl)-N,N-diethylamine (5.0 g, 26.93 mmol; preparation see: L. Strekowski, Pol. J. Chem. 1980, 54, 1557–62) in ethanol (200 ml) is heated at 100° C. for 16 hours. The mixture is then concentrated under reduced pressure and extracted with water/ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. Silica gel chromatography (mobile phase: dichloromethane/methanol) gives 4.01 g of the product (63%) as a yellow oil.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. extractionextracted with water/ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f68ac8464b644acbbd3c2eeddc8c60ff
Source dataset
uspto-grants-2006_10
Patent number
US07125995B2

Reaction notes

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