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

HRID 907529Notes

Reaction equation

HRID 907529 reaction equation
[Cl:1][CH:2]1[N:7](Cl)[CH:6]=[CH:5][N:4]=[CH:3]1.CN(C=O)C.[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]>O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86616579HCID 86616579, compound

Product 1

HCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 3,4-Dichloro-pyrazine (3 g, 20.1 mmol, 1.0 eq.), dry DMF (20 mL) and piperazine-1-carboxylic acid tert-butyl ester (7.3 g, 40 mmol, 2 eq). The reaction mixture was heated to 90° C. and allowed to stir for 4 hours. After allowing the reaction to return to room temperature water (100 mL) was added and the product extracted with DCM (2×200 mL). The organic layer was washed 1 N HCl (2×) and brine (2×) and dried over NaSO4. After removing the solvent the product was isolated as an orange oil (6 g, 80%).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customthe reaction
  3. customto return to room temperature
  4. additionwas added
  5. extractionthe product extracted with DCM (2×200 mL)
  6. washThe organic layer was washed 1 N HCl (2×) and brine (2×)
  7. dry with materialdried over NaSO4
  8. customAfter removing the solvent the product

Sources & evidence

ORD record
ord-e5b367023b9945c089135d2e0f7515a0
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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