Reaction #2329082

ord-08cc4a2109584cf6b78240fdbfd05f7a

Reaction equation

CCOC(C)=O.Cl
Hydrogen chloride ethyl acetate
CC(C)(C)OC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2F)CC1
4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylic acid tert-butyl ester
O=C([O-])O.[Na+]
sodium hydrogencarbonate
O=[N+]([O-])c1ccc(N2CCNCC2)c(F)c1
title compound
Yield 37.0%
O=[N+]([O-])c1ccc(N2CCNCC2)c(F)c1
1-(2-fluoro-4-nitrophenyl)piperazine
Yield 37.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated under reduced pressure
  2. 2
    FiltrationThe obtained solid was collected by filtration
  3. 3
    Washwashed with water

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07671058B2uspto-grants-2010_03