1-Piperazinecarboxylic acid, ethyl ester → HCID 22486153, compound

HRID 2181418Notes

Reaction equation

HRID 2181418 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])[CH3:13]>C(O)(C)C>[N+:9]([C:3]1[CH:4]=[CH:5][C:6]([N:20]2[CH2:19][CH2:18][N:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH2:22][CH2:21]2)=[N:7][C:2]=1[NH2:1])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 22486153HCID 22486153, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6-Amino-2-chloro-5-nitropyridine (Acros, 3.66 g 21 mmol) and 1-ethoxycarbonylpiperazine (6.36 g 42 mmol) in isopropanol (85 ml) are refluxed for 3 h. The reaction mixture with a yellow precipitate is poured on water/Na2CO3 and extracted twice with methylene chloride. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to yield the title compound as yellow crystals, which are purified by recrystallisation from tert.-butyl methyl ether (5.5 g 89%).

Workup

  1. additionThe reaction mixture with a yellow precipitate is poured on water/Na2CO3
  2. extractionextracted twice with methylene chloride
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5e30cdabf97f480fb332500780d7b814
Source dataset
uspto-grants-2005_05
Patent number
US06891039B2

Reaction notes

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