Reaction #157029

ord-7e48c55b25b54539b5ea005c80ce382d

Reaction equation

COc1ccc(Cl)c([N+](=O)[O-])c1
4-chloro-3-nitroanisole
CC(C)(C)OC(=O)N1CCNCC1
1-Boc-piperazine
→
COc1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)c([N+](=O)[O-])c1
tert-butyl 4-(4-methoxy-2-nitro phenyl)piperazine-1-carboxylate
Yield 50.0%

Reactants

COc1ccc(Cl)c([N+](=O)[O-])c1
4-chloro-3-nitroanisole
CC(C)(C)OC(=O)N1CCNCC1
1-Boc-piperazine
—
TEA

Reagents

None

Solvents

CN1CCCC1=O
NMP

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherat 100° C.
  2. 2
    Otherfor 16 hours

Procedure

Method 1 was followed using 4-chloro-3-nitroanisole (1.0 eq), 1-Boc-piperazine (1.2 eq), and TEA (2.0 eq) in NMP at 100° C. for 16 hours yielding tert-butyl 4-(4-methoxy-2-nitro phenyl)piperazine-1-carboxylate (50%). LCMS (m/z): 338.2 (MH+); LC Rt=3.37 min.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08822497B2uspto-grants-2014_09