tert-Butyl piperazine-1-carboxylate → HCID 86616580, compound

HRID 907545Notes

Reaction equation

HRID 907545 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].[Cl:14][C:15]1[N:16]=[C:17]([C:24]#[N:25])[C:18]([C:22]#[N:23])=[N:19][C:20]=1Cl>O1CCCC1>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:20]2[C:15]([Cl:14])=[N:16][C:17]([C:24]#[N:25])=[C:18]([C:22]#[N:23])[N:19]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 6078205,6-Dichloro-2,3-dicyanopyrazine

Product 1

HCID 86616580HCID 86616580, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

To a solution of 1-Boc-piperazine (8 mmol, 1.5 g) and anhydrous tetrahydrofuran cooled at −45° C. was added 5,6-dichloro-2,3-dicyanopyrazine (4 mmol, 800 mg). The mixture was stirred at −45° C. for 1.5 hours. Reaction mixture was concentrated and stirred in EtOAc, filtered and concentrated. The crude material was purified on silica column using 30% EtOAc/hexanes to yield 3′-Chloro-5′,6′-dicyano-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (640 mg).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. stirringstirred in EtOAc
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on silica column

Sources & evidence

ORD record
ord-c3e99e49890549928b60a76c6b547f94
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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