Piperazine → HCID 18186850, compound

HRID 1357588Notes

Reaction equation

HRID 1357588 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.ClCCl>[O:11]([CH2:10][CH2:9][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 18186845HCID 18186845, compound

Product 1

HCID 18186850HCID 18186850, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from step 1 above (1.29 g, 5.15 mmol), piperazine (1.30 g, 15.1 mmol) and K2CO3 (0.71 g, 5.14 mmol) in acetonitrile (5 mL) was heated in a sealed pyrex flask at 100° C. for 4 h. The reaction mixture was diluted with dichloromethane, filtered, and concentrated in vacuo. The light-brown semi-solid residue was purified by silica gel chromatography (15×4 cm) using CHCl3/MeOH (9:1) as eluent. Solvents were evaporated off and the residue was redissolved in ether/CHCl3 (1:1). Filtration and concentration in vacuo furnished 1.05 g (68%) of the title compound as a white solid. HRMS m/z calcd for C16H20N4O2 (M)+ 300.1586, found 300.1578. Anal. (C16H20N4O2) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe light-brown semi-solid residue was purified by silica gel chromatography (15×4 cm)
  4. customSolvents were evaporated off
  5. dissolutionthe residue was redissolved in ether/CHCl3 (1:1)
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-fb0086d1b07d45c89c34097f11fd049b
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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