p-Fluoronitrobenzene → HCID 58976363, compound

HRID 1050538Notes

Reaction equation

HRID 1050538 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3][CH2:2]1.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 47420041-Cyclopropylpiperazine

Product 1

HCID 58976363HCID 58976363, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-Cyclopropylpiperazine (268, 1.76 g, 14.0 mmol) was dissolved in 15 mL DMF. To it were added 1-fluoro-4-nitrobenzene (1.00 g, 7.0 mmol) and DIEA (1.24 mL, 7.0 mmol). The mixture was stirred at 90° C. for overnight, cooled to RT, diluted with EtOAc, washed with water ×2, dried, concentrated in vacuo, subjected to silica flash column using 0 to 40% EtOAc in DCM to isolate 1-cyclopropyl-4-(4-nitrophenyl)piperazine (269). It was dissolved in 2:1 EtOAc/MeOH (80 mL/40 mL), and to it were added 40 μL 6N HCl and 10% Pd/C (0.5 g). The mixture was stirred at RT for overnight under a hydrogen balloon. It was filtered through celite, concentrated in vacuo to dryness to afford 4-(4-cyclopropylpiperazin-1-yl)aniline hydrochloride (270, 1.30 g, 73% overall) as an off-white solid.

Workup

  1. temperaturecooled to RT
  2. washwashed with water ×2
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc55ce83ec1c4bdaaeeefa4030331037
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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