Potassium Carbonate → 7-(4-p-Tolyl-piperazin-1-ylmethyl)-chromen-2-one

HRID 581708

Reaction equation

HRID 581708 reaction equation
BrC[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8](=[O:13])[CH:7]=[CH:6]2.Cl.Cl.[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.[C:29](=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]1([CH3:28])[CH:17]=[CH:18][C:19]([N:22]2[CH2:23][CH2:24][N:25]([CH2:29][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][C:8](=[O:13])[O:9]4)=[CH:4][CH:3]=3)[CH2:26][CH2:27]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 831121-(p-Tolyl)piperazine dihydrochlorideHCID 105141316-Bromomethyl-chromen-2-one

Product 1

HCID 99495547-(4-p-Tolyl-piperazin-1-ylmethyl)-chromen-2-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-bromomethyl coumarin (0.5 g, 2.09 mmol), 4-tolylpiperazine dihydrochloride (0.51 g, 2.53 mmol) and potassium carbonate (2 g, 14.5 mmol) in acetonitrile (100 mL) was heated under reflux for 18 hours. The cooled mixture was filtered and concentrated under vacuum to provide a solid. Recrystallization from ethyl acetate provided the product as plates (0.45 g, 64% yield), mp 154-155° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe cooled mixture was filtered
  4. concentrationconcentrated under vacuum
  5. customto provide a solid
  6. customRecrystallization from ethyl acetate
  7. customprovided the product as plates (0.45 g, 64% yield), mp 154-155° C.

Sources & evidence

ORD record
ord-105eb17341314864bb8a29af18a87b74
Source dataset
uspto-grants-1999_07
Patent number
US05922719

Linked notes

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