2,6-Dibromopyridine → 4-Boc-1-(6-bromo-2-pyridyl)piperazine

HRID 2415166Notes

Reaction equation

HRID 2415166 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[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(N(CC)C(C)C)(C)C>C(O)CCC>[Br:8][C:4]1[N:3]=[C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4 g (16.88 mmol) of 2,6-dibromopyridine, 3.14 g (16.88 mmol) of tert.butyl piperazine-1-carboxylate and 5.89 ml (33.77 mmol) of N,N-diisopropylethylamine in 30 ml of n-butanol is refluxed for eight hours. The solvent is then distilled off. Purification is by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=2:1).

Workup

  1. distillationThe solvent is then distilled off
  2. customPurification

Sources & evidence

ORD record
ord-473ca581afe840cabcbaa3f57ff2a5a6
Source dataset
uspto-grants-2004_11
Patent number
US06818644B1

Reaction notes

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