1-Ethylpiperazine → HCID 58748501, compound

HRID 871878Notes

Reaction equation

HRID 871878 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=2)[CH2:17][CH2:16]1)[CH3:14]

Participants

5

Reactant 3

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 58748501HCID 58748501, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3.42 g (20 mmol) of 4-fluoro-2-methoxy-1-nitrobenzene, 2.67 mL (21 mmol) of 1-ethylpiperazine and 5.14 mL (30 mmol) of diisopropylethylamine in 25 mL of acetonitrile is heated for 2.5 hours at 85°C. and then for 1 hour at 95°C., and is then stirred overnight while allowing to return to room temperature. The acetonitrile is evaporated off and the residue is then taken up in 50 mL of ether and 25 mL of water. The aqueous phase is extracted with ether. The organic phases are combined, dried over Na2SO4, filtered and concentrated under vacuum. The oil obtained is triturated in an ether/cyclohexane mixture (1/1) and the precipitate is isolated by filtration, rinsed with pentane and dried in an oven. 4.1 g of the expected product are finally obtained. Yield=77%.

Workup

  1. customto return to room temperature
  2. customThe acetonitrile is evaporated off
  3. extractionThe aqueous phase is extracted with ether
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe oil obtained
  8. customis triturated in an ether/cyclohexane mixture (1/1)
  9. customthe precipitate is isolated by filtration
  10. washrinsed with pentane
  11. customdried in an oven

Sources & evidence

ORD record
ord-21d2b592da1e44c8bd082271dee638c2
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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