Potassium Carbonate → Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

HRID 353708Notes

Reaction equation

HRID 353708 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[C:26](Cl)=[N:25][CH:24]=[CH:23][N:22]=1>C(#N)C>[Cl:20][C:21]1[C:26]([N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)=[N:25][CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared according to the procedure described in WO 00/76984. A mixture of N-Boc-piperazine (11.47 g, 61.5 mmol), K2CO3 (8.5 g, 61 mmol) and 2,3-dichloropyrazine (9.20 g, 61.7 mmol) in acetonitrile (100 mL) was stirred at 100° C. for 40 h. The reaction mixture was concentrated, dissolved in toluene, washed with water, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel using toluene/EtOAc (7:3) as eluent to give 18.3 g (100%) of the title product. HRMS m/z calcd for C13H19N4O2 (M)+298.1197, found 298.1206.

Workup

  1. customThe title compound was prepared
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in toluene
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-aa6bc45816e348b0828a17b137e94677
Source dataset
uspto-grants-2004_06
Patent number
US06756377B2

Reaction notes

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