Acetic Acid → tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

HRID 2236413Notes

Reaction equation

HRID 2236413 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][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)=[N:8][CH:9]=1)([O-])=O.C(O)(=O)C>CO.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][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)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate (0.5 g, 1.62 mmol), iron powder (0.35 g, 6.26 mmol), acetic acid (0.72 mL, 11.34 mmol) in methanol (6 mL) is heated at 66 C for 1 h. After it is evaporated to dryness, ethyl acetate is added, and then the mixture is filtered through a pad of Celite. The filtrate is evaporated to yield 0.32 g (72%) of the title compound as an orange gum. NMR (CDCl3) spectrum of the product showed it is pure.

Workup

  1. temperatureis heated at 66 C for 1 h
  2. customAfter it is evaporated to dryness, ethyl acetate
  3. additionis added
  4. filtrationthe mixture is filtered through a pad of Celite
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-badf95f6558f472293f489f366504509
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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