2,6-Dichloropyrazine → Tert-butyl 4-(6-chloropyrazin-2-YL)piperazine-1-carboxylate

HRID 2376654Notes

Reaction equation

HRID 2376654 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:20]=[N:19][CH:18]=[C:17](Cl)[N:16]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:14][C:15]1[N:16]=[C:17]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:18]=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 785042,6-DichloropyrazineHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18186946Tert-butyl 4-(6-chloropyrazin-2-YL)piperazine-1-carboxylateYield 58.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 5 g of tert-butyl 1-piperazinecarboxylate, 4 g of 2,6-dichloropyrazine and 9.5 ml de DIPEA in 40 ml of n-butanol is heated at reflux for 3 hours. It is concentrated under vacuum, the residue is taken up in 100 ml of EtOH, the system is left to stand overnight and the crystalline product formed is isolated with suction. This gives 4.7 g of the expected product, m.p.=108° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. concentrationIt is concentrated under vacuum
  4. waitthe system is left
  5. customthe crystalline product formed
  6. customis isolated with suction

Sources & evidence

ORD record
ord-62289463b0af43f390207bb8cbb98749
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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