Piperazine → 2-(2-Furyl)-6-(1-Piperazinyl)Pyrazine

HRID 1296622Notes

Reaction equation

HRID 1296622 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.ClCCl.C(Cl)(Cl)Cl.CCOCC>[O:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:3]=1

Participants

7

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 181868472-Chloro-6-(2-Furyl)Pyrazine

Product 1

HCID 181868482-(2-Furyl)-6-(1-Piperazinyl)PyrazineYield 64%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 21911965Chloroform etherSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the product from step 1 above (0.94 g, 5.2 mmol), piperazine (1.28 g, 14.9 mmol, K2CO3 (0.87 g, 6.3 mmol) in acetonitrile (5 mL) was heated in a sealed pyrex flask at 85° C. for 3 h. The mixture was diluted with dichloromethane, filtered, and concentrated in vacuo. The oily residue was purified by silica gel chromatography (18×4 cm) to furnish a yellow oil. This material was redissolved in a small volume of CHCl3/ether (9:1) and filtered through a short (4 cm) plug of alumina eluting with ether/MeOH (96:4). The filtrate was concentrated in vacuo to afford 0.77 g (64%) of the title compound as a light yellow solid. HRMS m/z calcd for C12H14N4O (M)+ 230.1168, found 230.1170. Anal. (C12H14N4O) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe oily residue was purified by silica gel chromatography (18×4 cm)
  4. customto furnish a yellow oil
  5. filtrationfiltered through a short (4 cm) plug of alumina eluting with ether/MeOH (96:4)
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7f9d67874e7148f0af6cacbfa8eefd2e
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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