Piperazine → HCID 22036461, compound

HRID 1789692Notes

Reaction equation

HRID 1789692 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[C:14]1[C:15]([O:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=2)=[N:16][CH:17]=[CH:18][N:19]=1>C(#N)C>[N:1]1([C:14]2[C:15]([O:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=3)=[N:16][CH:17]=[CH:18][N:19]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 22036247HCID 22036247, compound

Product 1

HCID 22036461HCID 22036461, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperazine (1.29 g, 15.0 mmol) and K2CO3 (0.69 g, 5.0 mmol) were added to a solution of 2-(3-bromophenoxy)ethyl 3-chloro-2-pyrazinyl ether (1.65 g, 5.00 mmol) in acetonitrile (25 mL) at room temperature. The mixture was heated at reflux for 21 h, allowed to cool, concentrated and the residue was partitioned between water and EtOAc. The layers were separated and the organic phase was washed with water and brine, and dried over MgSO4. Purification by chromatography on silica gel (gradient: PhMe to PhMe/MeOH/Et3N, 8:1:1) gave 1.61 g (85%) of the title compound as a pale yellow oil that slowly solidified on standing: mp 62-63° C. Anal. (C16H19BrN4O2) C, H, N.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 21 h
  3. temperatureto cool
  4. concentrationconcentrated
  5. customthe residue was partitioned between water and EtOAc
  6. customThe layers were separated
  7. washthe organic phase was washed with water and brine
  8. dry with materialdried over MgSO4
  9. customPurification by chromatography on silica gel (gradient: PhMe to PhMe/MeOH/Et3N, 8:1:1)

Sources & evidence

ORD record
ord-3aaf611856bb4041a612001264e3dbc8
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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