1-Fluoro-3-nitrobenzene → Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate

HRID 513283Notes

Reaction equation

HRID 513283 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>CS(C)=O>[N+:8]([C:4]1[CH:3]=[C:2]([N:21]2[CH2:20][CH2:19][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:23][CH2:22]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 98231-Fluoro-3-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22330126Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylateYield 33.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-fluoronitrobenzene (2 mL, 18.8 mmol) in DMSO (20 mL) was added Boc-piperazine (10 g, 56.4 mmol), after stirring at 100° C. for 3 days, the mixture was poured to ice water, the resulting precipitate was collected by filtration to give tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate (1.91 g).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-3970f499b7be4a94a6d0505339b2eead
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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