Acetic Acid → tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

HRID 2236530Notes

Reaction equation

HRID 2236530 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>[Fe].CO>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 11243758Tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

An amount of 2 g (6.48 mmol) of, tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, 1.4 g (25.9 mmol) of iron, and acetic acid (3.1 mL, 48.6 mmol) were placed in a flask. Methanol (30 mL) is added and heat at 60° C. for 2 hours. After cooling to room temperature, the precipitate is filtered, the methanol is removed in a vacuum and saturated sodium bicarbonate is added. The mixture is extracted 3× with ethyl acetate. Dried over sodium sulfate, and evaporated to give 1.43 g (78% yield) as a purple solid. MS (ESI) m/z 279.1(M+1)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate is filtered
  3. customthe methanol is removed in a vacuum and saturated sodium bicarbonate
  4. additionis added
  5. extractionThe mixture is extracted 3× with ethyl acetate
  6. dry with materialDried over sodium sulfate
  7. customevaporated
  8. customto give 1.43 g (78% yield) as a purple solid

Sources & evidence

ORD record
ord-a577fbe06cf34ffe9f29ac8e6e683495
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…