Piperazine → HCID 18186921, compound

HRID 1357583Notes

Reaction equation

HRID 1357583 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=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(OCC)(=O)C>[N:13]1([C:2]2[CH:7]=[N:6][CH:5]=[C:4]([C:8]3[CH:12]=[CH:11][S:10][CH:9]=3)[N:3]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

7

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 18186818HCID 18186818, compound

Product 1

HCID 18186921HCID 18186921, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the product from step 1 above (1.04 g, 5.29 mmol), piperazine (1.32 g, 15.3 mmol), and K2CO3 (0.81 g, 5.82 mmol) in acetonitrile (6 mL) was heated in a sealed pyrex flask at 85° C. for 8.5 h. The reaction mixture was diluted with dichloromethane, filtered, and concentrated in vacuo. The semi-solid residue was purified by column chromatography on silica gel (18×5 cm) using CHCl3/MeOH (9:1) as eluent to furnish an oil. This material was redissolved in ethyl acetate, filtered, and concentrated in vacuo. This gave 0.98 g (75%) of the title compound as a yellow sticky oil. HRMS m/z calcd for C12H14N4S (M)+ 246.0939, found 246.0943. Anal. (C12H14N4S) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe semi-solid residue was purified by column chromatography on silica gel (18×5 cm)
  4. customto furnish an oil
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76f40c2864f24a918c67f569d0fb50a8
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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