Dimethylformamide → HCID 22031072, compound

HRID 1792433Notes

Reaction equation

HRID 1792433 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 22031072HCID 22031072, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 485 mg 6-bromo-4-chloroquinoline, 1.1 mL N-methyl piperazine, 415 mg potassium carbonate and 10 mL N,N-dimethylformamide was stirred at 130° C. for 8 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and brine and dried over an hydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 502 mg of the title compound as pale yellow crystals.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over an hydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-826001f3bb384ba3ae1349f678af87ac
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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