Sodium Carbonate → Tert-butyl 4-(6-chloropyrazin-2-YL)piperazine-1-carboxylate

HRID 2182129Notes

Reaction equation

HRID 2182129 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[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].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)(C)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18186946Tert-butyl 4-(6-chloropyrazin-2-YL)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 2,6-dichloropyrazine (2.98 g, 20 mmol), piperazine-1-carboxylic acid tert-butyl ester (3.72 g, 20 mmol) and sodium carbonate (2.12 g, 20 mmol) in t-butanol (50 mL) was heated at reflux under nitrogen for 65 h. The solution was concentrated in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous phase was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to give the title compound (I-1a) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 65 h
  3. concentrationThe solution was concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
  6. washThe combined organic extracts were washed with brine (50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-951f6c0aa84b49b59156874716f3f2ff
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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