Potassium Carbonate → 1-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline

HRID 1006881Notes

Reaction equation

HRID 1006881 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Br:12])[N:3]=1.[CH2:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:12][C:4]1[N:3]=[C:2]([N:18]2[CH2:19][CH2:20][N:15]([CH2:13][CH3:14])[CH2:16][CH2:17]2)[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 6409761,3-Dibromoisoquinoline

Product 1

HCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3-Dibromoisoquinoline (2.70 g), N-ethylpiperazine (1.16 g) and potassium carbonate (3.50 g) were reacted in DMF (30 ml) at 80° C. for 5 hr. The reaction solution was evaporated, and then partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried and evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give the title compound (2.21 g) as a pale yellow oil.

Workup

  1. customThe reaction solution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. washThe resulting organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

Sources & evidence

ORD record
ord-e0b09efcce7647b2afdd681244b46399
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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