2-Bromopyridine → 1-[N-(2-nitrophenyl)-N-(2-pyridyl)-2-aminoethyl]-4-(2-methoxyphenyl)-piperazine

HRID 2181637Notes

Reaction equation

HRID 2181637 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:15][CH2:14]1)([O-:3])=[O:2].Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:17][CH2:18]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 79732-Bromopyridine2×HCID 11430Potassium CarbonateHCID 224820891-[N-(2-nitrophenyl)-2-aminoethyl]-4-(2-methoxyphenyl)piperazine

Product 1

HCID 224820921-[N-(2-nitrophenyl)-N-(2-pyridyl)-2-aminoethyl]-4-(2-methoxyphenyl)-piperazineYield 52%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
160 °C

Procedure

A mixture of 0.43 g of 1-[N-(2-nitrophenyl)-2-aminoethyl]-4-(2-methoxyphenyl)piperazine (prepared as described in U.S. Pat. No. 3,472,854), 0.19 g of 2-bromopyridine, 0.17 g of anhydrous potassium carbonate and 0.01 g of powdered copper was heated to 100° C., and maintained at that temperature for 3 h, followed by the addition of another 0.138 g of 2-bromopyridine, and the heating of the mixture to 160° C. for 24 h. After cooling the mixture to room temperature and extraction with ethyl acetate (2×20 mL), the combined organic phases were then washed with water, dried on sodium sulphate, and evaporated to dryness in vacuo. The obtained crude was next purified by flash chromatography (ethyl acetate-petroleum ether 7:3). The recovered fractions, after evaporation to dryness, afforded 0.25 g of the compound of Example 11 (52%).

Workup

  1. customprepared
  2. temperaturemaintained at that temperature for 3 h
  3. temperatureAfter cooling the mixture to room temperature
  4. extractionextraction with ethyl acetate (2×20 mL)
  5. washthe combined organic phases were then washed with water
  6. customdried on sodium sulphate
  7. customevaporated to dryness in vacuo
  8. customThe obtained crude
  9. customwas next purified by flash chromatography (ethyl acetate-petroleum ether 7:3)
  10. customThe recovered fractions, after evaporation to dryness

Sources & evidence

ORD record
ord-7f5af836c519402a86cf7a3df0fcf6ed
Source dataset
uspto-grants-2005_05
Patent number
US06894052B1

Reaction notes

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