Piperazine → HCID 18186867, compound

HRID 1296630Notes

Reaction equation

HRID 1296630 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]=[CH:13][CH:12]=2)[CH3:10])[N:3]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.ClCCl>[C:11]1([CH:9]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:3]=2)[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 18186821HCID 18186821, compound

Product 1

HCID 18186867HCID 18186867, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product from step 1 above (1.53 g, 6.5 mmol), piperazine (1.62 g, 18.9 mmol) and K2CO3 (0.90 g, 6.5 mmol) in acetonitrile (6 mL) was heated in a sealed pyrex flask at 90° C. for 3.5 h. The reaction mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The semi-solid residue was purified by silica gel chromatography (13×4 cm) using CHCl3/MeOH (9:1) as eluent. Solvents were evaporated off and the remaining oil was redissolved in CHCl3, filtered through a short plug of alumina and concentrated in vacuo. This gave 1.34 g (72%) of the title compound as an oil that solidified when refrigerated. HRMS m/z calcd for C16H20N4O (M)+ 284.1637, found 284.1650. Anal. (C16H20N4O.C4H4O4) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe semi-solid residue was purified by silica gel chromatography (13×4 cm)
  4. customSolvents were evaporated off
  5. dissolutionthe remaining oil was redissolved in CHCl3
  6. filtrationfiltered through a short plug of alumina
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78f933a3588f4d20b462a2cb6d9d583c
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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