Piperazine → N-(1-Methylethyl)-3-(1-piperazinyl)-2-pyrazinamine

HRID 864392Notes

Reaction equation

HRID 864392 reaction equation
Cl[C:2]1[C:7]([NH:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:5]=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C1(C)C(C)=CC=CC=1.Cl>[CH3:10][CH:9]([NH:8][C:7]1[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:3][CH:4]=[CH:5][N:6]=1)[CH3:11]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 214776373-Chloro-N-(propan-2-yl)pyrazin-2-amine

Product 1

HCID 21477657N-(1-Methylethyl)-3-(1-piperazinyl)-2-pyrazinamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 2-chloro-3-(1-methylethylamino)pyrazine (PREPARATION 24, 1.6 g) and piperazine (4.3 g) in xylene (10 ml) is refluxed for 26 hr. The mixture is cooled to 0o and diluted with concentrated hydrochloric acid (8 ml). The xylene is decanted and ether is added and also decanted from the salts. The salts are diluted with excess aqueous sodium hydroxide (5%) and dichloromethane. The phases are separated. The aqueous phase is extracted three more times with dichloromethane. The combined organic extracts are dried over sodium sulfate and concentrated to give a liquid mixture which is flash chromatographed on silica gel eluting with methanol/chloroform (5/95). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.27, 1.83, 3.04, 4.12, 4.78, 7.49 and 7.72δ.

Workup

  1. customThe xylene is decanted
  2. additionether is added
  3. customalso decanted from the salts
  4. additionThe salts are diluted with excess aqueous sodium hydroxide (5%) and dichloromethane
  5. customThe phases are separated
  6. extractionThe aqueous phase is extracted three more times with dichloromethane
  7. dry with materialThe combined organic extracts are dried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a liquid mixture which
  10. customchromatographed on silica gel eluting with methanol/chloroform (5/95)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7f6c8ed228e642e8aca1be0ffda95c44
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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