Piperazine → HCID 66758722, compound

HRID 564225Notes

Reaction equation

HRID 564225 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].N1CCNCC1>O.O1CCOCC1>[CH3:15][O:14][C:12]([C:10]1[S:11][C:7]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][N:1]2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[CH:8][CH:9]=1)=[O:13]

Participants

7

Reactant 4

HCID 4837PiperazineHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 66759646HCID 66759646, compound

Product 1

HCID 66758722HCID 66758722, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of EXAMPLE 28B (0.3 g), potassium carbonate (0.36 g), dioxane (20 mL) and water (5 mL) was added benzyl chloroformate (0.23 mL), and the mixture stirred for 4 hours. Piperazine was added, and the mixture stirred for 30 minutes and partitioned between ethyl acetate and brine. The extract was washed with brine, dried over magnesium sulfate, filtered and concentrated. The concentrate was flash chromatographed on silica gel with 10-50% ethyl acetate in hexane.

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. custompartitioned between ethyl acetate and brine
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel with 10-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6e0d0315c47d431f83129758df971135
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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