Sodium Carbonate → 4-Boc-1-(5-bromo-2-pyridyl)piperazine

HRID 393706Notes

Reaction equation

HRID 393706 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[C:18]([O:17][C:15]([N:9]1[CH2:14][CH2:13][N:12]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH2:11][CH2:10]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 112447754-Boc-1-(5-bromo-2-pyridyl)piperazineYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In pre-dried apparatus, held under a CaCl2 guard tube, 2,5-dibromopyridine (0.524 g), tert-butyl piperazine-1-carboxylate (0.824 g) and sodium carbonate (0.234 g) were combined in anhydrous 1-methyl-2-pyrrolidinone (10 ml) and heated in an oil bath held at 100° C. for 4 days. The mixture was then cooled, poured onto water (350 ml) and extracted with diethyl ether (3×50 ml). The combined organic extracts were washed with 2% citric acid solution (2×25 ml), water (2×25 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure. The residue was then purified by silica gel column chromatography, with 30% diethyl ether/hexane as eluent, to provide the title compound as a white solid (0.537 g, 71%).

Workup

  1. temperatureheated in an oil bath
  2. temperatureThe mixture was then cooled
  3. additionpoured onto water (350 ml)
  4. extractionextracted with diethyl ether (3×50 ml)
  5. washThe combined organic extracts were washed with 2% citric acid solution (2×25 ml), water (2×25 ml), saturated brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe residue was then purified by silica gel column chromatography, with 30% diethyl ether/hexane as eluent

Sources & evidence

ORD record
ord-38822d3a659f460db67ed7f112792a2c
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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