1-Cyclopropylpiperazine → HCID 67325292, compound

HRID 871866Notes

Reaction equation

HRID 871866 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[CH:15]1([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:17][CH2:16]1>C(#N)C>[CH:15]1([N:18]2[CH2:23][CH2:22][N:21]([C:8]3[CH:7]=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[C:4]([O:3][CH:2]([F:14])[F:1])[CH:9]=3)[CH2:20][CH2:19]2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 47420041-CyclopropylpiperazineHCID 463115882-(Difluoromethoxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 67325292HCID 67325292, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To 2.07 g (10.0 mmol) of the product prepared in step 14.1 in 30 mL of acetonitrile are added 5.99 mL (35.0 mmol) of diispropylethylamine and then 2.09 g (10.5 mmol) of finely ground N-cyclopropylpiperazine (supplier). The reaction mixture is heated at 100°C. for 1 hour 30 minutes, cooled and concentrated under vacuum. The residue is taken up in 75 mL of ethyl acetate and washed with saturated aqueous NaHCO3 solution and with saturated aqueous NaCl solution. The organic phase is dried over Na2SO4, filtered and concentrated under vacuum. After triturating in cyclohexane, the solid is drained by suction and dried in an oven under vacuum. 2.33 g of the expected product are obtained in the form of a yellow solid, which is used as obtained in the following step. Yield=74.5%.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. washwashed with saturated aqueous NaHCO3 solution and with saturated aqueous NaCl solution
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customAfter triturating in cyclohexane
  8. customdried in an oven under vacuum

Sources & evidence

ORD record
ord-18c0cf8960cc40a48365fed5a5882b76
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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