1-Fluoro-2-nitrobenzene → 1-Boc-4-(2-nitrophenyl)piperazine

HRID 69834Notes

Reaction equation

HRID 69834 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[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]>CCO>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:21]1[CH2:20][CH2:19][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:23][CH2:22]1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 219352101-Boc-4-(2-nitrophenyl)piperazineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method of Example 1 was followed using 1-fluoro-2-nitrobenzene (1.0 eq), 1-Boc-piperazine (1.2 eq), and TEA (2.0 eq) in EtOH at 55° C. for 72 hours yielding tert-butyl 4-(2-nitro phenyl)piperazine-1-carboxylate (100%). LCMS (m/z): 308.1 (MH+); LC Rt=3.25 min.

Workup

  1. customat 55° C.
  2. customfor 72 hours

Sources & evidence

ORD record
ord-ca4e9a2d63954b809a835994db004818
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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