Sodium Bicarbonate → 1-(2-fluoro-4-nitrophenyl)piperazine

HRID 2241900Notes

Reaction equation

HRID 2241900 reaction equation
Cl.C(OCC)(=O)C.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=2[F:30])[CH2:17][CH2:16]1)=O)(C)(C)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[F:30][C:22]1[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=1[N:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 16203508tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 27830661-(2-fluoro-4-nitrophenyl)piperazineYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4N Hydrogen chloride/ethyl acetate solution (10.0 ml, 40.0 mmol) was added to a solution of 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylic acid tert-butyl ester (compound of Reference Example 14; 2.50 g, 7.68 mmol) in ethyl acetate (10 ml) under ice cooling, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was adjusted to pH=9 by addition of saturated aqueous sodium hydrogencarbonate, and concentrated under reduced pressure. The obtained solid was collected by filtration and washed with water to give the title compound (0.563 g, 37%) as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe obtained solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-08cc4a2109584cf6b78240fdbfd05f7a
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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