Piperazine → 1-(3-Nitrophenyl)piperazine

HRID 479991Notes

Reaction equation

HRID 479991 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>CN1C(=O)CCC1.O>[N+:8]([C:4]1[CH:3]=[C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 98231-Fluoro-3-nitrobenzene

Product 1

HCID 27602161-(3-Nitrophenyl)piperazineYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 3-fluoronitrobenzene (23 ml; 0.21 mol) and piperazine (55.5 g; 0.64 mol) in anhydrous NMP (30 ml) was heated to 70° C. for five days. The cooled mixture was diluted with water (250 ml) and extracted with dichloromethane. The combined extracts were dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column-chromatography on silica gel eluting subsequently with mixtures of ethyl acetate and methanol (4:1 v/v) and (1:1 v/v) to leave the desired product as oily crystals (30.7 g; 71%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column-chromatography on silica gel eluting subsequently with mixtures of ethyl acetate and methanol (4:1 v/v) and (1:1 v/v)

Sources & evidence

ORD record
ord-719bd51a8d744837a1e2003b26272f1c
Source dataset
uspto-grants-2003_11
Patent number
US06649609B2

Reaction notes

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