Piperazine → 2-[1-(3-FLUOROPHENYL)ETHOXY]-6-(1-PIPERAZINYL)PYRAZINE

HRID 1296606Notes

Reaction equation

HRID 1296606 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH3:10])[N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C(#N)C.O>[F:17][C:13]1[CH:12]=[C:11]([CH:9]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[N:3]=2)[CH3:10])[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 113911202-chloro-6-[1-(3-fluorophenyl)ethoxy]pyrazine

Product 1

HCID 98178662-[1-(3-FLUOROPHENYL)ETHOXY]-6-(1-PIPERAZINYL)PYRAZINEYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of the product from step 1 above (crude, 1.09 g, ˜4.3 mmol), piperazine (1.03 g, 12.0 mmol) and K2CO3 (1.00 g, 7.2 mmol) in acetonitrile (5 mL) was heated under reflux overnight (20 h). After cooling, ethyl acetate (15 mL) and water (5 mL) were added. The ethyl acetate layer was filtered through a short column of silica gel using MeOH/ethyl ether (1:1) as eluent to give 0.72 g (55%) of the title compound as an oil. HRMS m/z calcd for C16H19N4O4F (M)+ 302.1543, found 302.1528. Anal. (C16H19N4OF.0.5 H2O) C, H, N.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight (20 h)
  3. temperatureAfter cooling
  4. filtrationThe ethyl acetate layer was filtered through a short column of silica gel

Sources & evidence

ORD record
ord-ab2a792cdfbd44aeb6499d3ac996f2c6
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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