Piperazine → HCID 12016523, compound

HRID 411250Notes

Reaction equation

HRID 411250 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(=O)CC.C(OCC)(=O)C>[OH-:5].[NH4+:23].[CH:14]1([C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:7][CH:8]=2)=[O:13])[CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 12016522HCID 12016522, compound

Product 2

HCID 14923Ammonium HydroxideHCID 12016523HCID 12016523, compoundYield 164%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 1B (10 g, 42 mmol), KI (8.5 g, 51.2 mmol), K2CO3 (8.75 g, 63.3 mmol), and piperazine (10.75 g, 125 mmol) in 2-butanone (500 mL) was refluxed for 48 hours. The reaction mixture was then cooled to room temperature, treated with 1 M sodium thiosulfate (100 mL) and ethyl acetate (500 mL). The layers were separated, and the organic layer was washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by column chromatography on silica gel using 98:2:0.1 to 95:5:0.9 dichloromethane:methanol:concentrated ammonium hydroxide as the eluant to afford 9.931 g (82%) of the desired product.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography on silica gel using 98:2:0.1 to 95:5:0.9 dichloromethane

Sources & evidence

ORD record
ord-60a7738f4c1b412eaa534dfa47f0013b
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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