Triethylamine → tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylate

HRID 2236412Notes

Reaction equation

HRID 2236412 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:21]2[CH2:20][CH2:19][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:23][CH2:22]2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 782402-Bromo-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-5-nitro-pyridine (1.719 g, 8.468 mmol), piperazine-1-carboxylic acid tert-butyl ester (1.58 g, 8.468 mmol), triethylamine (3.54 mL, 25.4 mmol) in acetonitrile (6 mL) is heated at 86 C for 2 h. After it is evaporated, the residue is dissolved in methylene chloride, and washed with saturated sodium bicarbonate solution. The organic layer is evaporated to yield 2.6 g (99%) of the title compound as a pale-yellow solid. NMR (CDCl3) showed it is pure.

Workup

  1. temperatureis heated at 86 C for 2 h
  2. customAfter it is evaporated
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washwashed with saturated sodium bicarbonate solution
  5. customThe organic layer is evaporated

Sources & evidence

ORD record
ord-3c9e12781b1c46bd9779d66e85db08fc
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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