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Water → 4-(5-Nitropyridin-2-yl)piperazin-2-one

HRID 1020350
Notes
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Reaction equation

HRID 1020350 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[O:20]=[C:21]1[CH2:26][NH:25][CH2:24][CH2:23][NH:22]1.O>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:25]2[CH2:24][CH2:23][NH:22][C:21](=[O:20])[CH2:26]2)=[N:3][CH:4]=1)([O-:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 231360Piperazin-2-one

Product 1

HCID 165609144-(5-Nitropyridin-2-yl)piperazin-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (623 mg, 3.9 mmol) in DMF (6 mL) was added N,N-diisopropylethylamine (1.4 mL, 8.5 mmol) and 2-oxopiperazine (424 mg, 4.24 mmol). The reaction mixture was heated at 85° C. for 40 min by microwave. Then the reaction mixture was cooled to RT, and poured into water (150 mL). The precipitate was filtered, washed with water and dried under vacuum to yield 4-(5-nitropyridin-2-yl)piperazin-2-one as a solid (588 mg, 68% yield). MS (M+1): 223.3

Workup

  1. temperatureThen the reaction mixture was cooled to RT
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ed8316c17b304396a7b74b2786914d4c
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716312B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes