Triethylamine → 4-(3-Nitropyrazin-2-yl)piperazin-2-one

HRID 2291017Notes

Reaction equation

HRID 2291017 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17].C(N(CC)CC)C>C(Cl)(Cl)Cl.C(O)(C)C>[N+:8]([C:7]1[C:2]([N:14]2[CH2:15][CH2:16][NH:11][C:12](=[O:17])[CH2:13]2)=[N:3][CH:4]=[CH:5][N:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 231360Piperazin-2-oneHCID 159142352-Chloro-3-nitropyrazine

Product 1

HCID 137486294-(3-Nitropyrazin-2-yl)piperazin-2-oneYield 54.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-chloro-3-nitropyrazine (9.1 g, 57 mmol) in chloroform (100 ml) was added dropwise over 45 minutes to a cooled solution of piperazine-2-one (5.71 g, 57 mmol) and triethylamine (8.0 ml, 57 mmol) in isopropanol (120 ml). After addition was complete, the reaction mixture was allowed to warm to 20°-25° and was stirred at this temperature for 20 hours. The precipitate was removed by filtration and recrystallized from methanol-ethyl acetate-hexane to give 6.96 g (54.7%) of product, m.p. 178°-179°.

Workup

  1. additionAfter addition
  2. temperatureto warm to 20°-25°
  3. customThe precipitate was removed by filtration
  4. customrecrystallized from methanol-ethyl acetate-hexane

Sources & evidence

ORD record
ord-d43492dae2274d8c9f5c5cd4471f5bb0
Source dataset
uspto-grants-1986_10
Patent number
US04619927

Reaction notes

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