2,5-Dibromopyridine → 4-Boc-1-(5-bromo-2-pyridyl)piperazine

HRID 1158712Notes

Reaction equation

HRID 1158712 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>N1C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:19]2[CH2:18][CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:21][CH2:20]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

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

Product 1

HCID 112447754-Boc-1-(5-bromo-2-pyridyl)piperazineYield 39.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixed solution of 2,5-dibromopyridine (6.36 g, 26.8 mmol), 1-(tert-butoxycarbonyl)piperazine (5.00 g, 26.8 mmol) and pyridine (100 ml) was stirred at 125° C. for 12 hours, and the solvent was distilled away under reduce pressure. The residue was poured into water, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give the titled compound 3.62 g (39.5%) as solid product.

Workup

  1. distillationthe solvent was distilled away
  2. additionThe residue was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-167f1c144cb44fec8e237df97a39f0f2
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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