Water → HCID 16560914, compound

HRID 1020350Notes

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]

Participants

6

Reactant 4

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

Product 1

HCID 16560914HCID 16560914, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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
Patent number
US08716312B2

Reaction notes

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