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

HRID 1789699Notes

Reaction equation

HRID 1789699 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

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

Sources & evidence

ORD record
ord-0ad0051db2c74da4bf97b6fb09b1e0f3
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

Loading…