2-Bromo-4-phenylpyridine → Tert-butyl 4-(4-phenylpyridin-2-yl)piperazine-1-carboxylate

HRID 1158707Notes

Reaction equation

HRID 1158707 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1>[C:8]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:24]3[CH2:23][CH2:22][N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:26][CH2:25]3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1047002-Bromo-4-phenylpyridineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 68644576Tert-butyl 4-(4-phenylpyridin-2-yl)piperazine-1-carboxylateYield 20.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-bromo-4-phenylpyridine (1.34 g, 5.72 mmol), 1-(tert-butoxycarbonyl)piperazine (3.19 g, 17.2 mmol) and pyridine (20 ml) was stirred at 125° C. for 7 days, and the solvent was distilled away under reduce pressure. To the residue was added water, and extracted with ethyl acetate. The extract was washed with water, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the titled compound 390 mg (20.1%) as solid product.

Workup

  1. distillationthe solvent was distilled away
  2. additionTo the residue was added water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. distillationthe solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ce58f09de14b471cae6210ff0e695b82
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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