1-Ethylpiperazine → 6-Bromo-8-(1-ethylpiperazin-4-yl)-1,7-naphthyridine

HRID 1251157Notes

Reaction equation

HRID 1251157 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Br)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:18]3[CH2:19][CH2:20][N:15]([CH2:13][CH3:14])[CH2:16][CH2:17]3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 791961-EthylpiperazineHCID 225032286,8-Dibromo-1,7-naphthyridine

Product 1

HCID 225032736-Bromo-8-(1-ethylpiperazin-4-yl)-1,7-naphthyridineYield 98%

Conditions

Temperature
100 °C

Procedure

6,8-Dibromo-1,7-naphthyridine (3.464 g) was added to 1-ethylpiperazine (10 ml), and the resulting mixture was stirred at 100° C. for 15 min. The reaction mixture was evaporated, and then partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellowish orange solid (3.780 g, yield; 98%).

Workup

  1. customThe reaction mixture was evaporated
  2. custompartitioned between ethyl acetate and water
  3. washThe resulting organic layer was washed with water
  4. dry with materialdried (over MgSO4)
  5. customevaporated
  6. customThe resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-b62cc567fc674a359b050b04cd825e19
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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