2,3-Dichloropyrazine → Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

HRID 1045706Notes

Reaction equation

HRID 1045706 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[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)C>[Cl:8][C:7]1[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)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 785752,3-DichloropyrazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mL round bottom flask was charged with 2,3-dichloropyrazine (10.0 g, 67.1 mmol), tert-butyl piperazine-1-carboxylate (25.0 g, 134 mmol) and ethanol (200 mL). The resulting solution was heated at reflux overnight. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel with 5%-10% EtOAc in petroleum ether, to afford 14.0 g (70%) of the product as a white solid. 1H NMR (300 MHz, CDCl3) δ: 8.08 (d, J=2.4 Hz, 1H), 7.87 (d, J=2.4 Hz, 1H), 3.55 (m, 4H), 3.38 (m, 4H), 1.45 (s, 9H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash column chromatography on silica gel with 5%-10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-4a348db7f5794ca788d5080df3d204f0
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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