Piperazine → 1-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine

HRID 1261893Notes

Reaction equation

HRID 1261893 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[C:20](#N)C.C(=O)([O-])[O-].[K+].[K+]>>[CH3:20][N:14]1[CH2:19][CH2:18][N:17]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 4837PiperazineHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2359871-(2-Bromoethoxy)-4-nitrobenzene

Product 1

HCID 128308431-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine

Conditions

Temperature
80 °C

Procedure

Into a 30 mL vial, 1-(2-Bromo-ethoxy)-4-nitro-benzene (5.00 g, 0.0203 mol), piperazine, 1-methyl-(4.51 mL, 0.0406 mol), Acetonitrile (15.0 mL, 0.287 mol) and Potassium carbonate (5.62 g, 0.0406 mol) were added. The reaction was heated at 80° C. for 4 hours. The reaction was partitioned with water and extracted with Et2O (3×100 mL). The Combined organic was washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum to afford 1-Methyl-4-[2-(4-nitro-phenoxy)-ethyl]-piperazine as an off white solid (3.89 g, 73%). NMR 1H (DSMO-d6-8.20 (dd, 2H, JJ=2.04, 5.12 Hz), 7.16 (dd, 2H, JJ=2.04, 5.08 Hz), 4.22 (t, 2H, J=5.76 Hz), 2.71 (t, 2H, J=5.72 Hz), 2.18-2.6 (bm, 8H), 2.13 (s, 3H)

Workup

  1. customThe reaction was partitioned with water
  2. extractionextracted with Et2O (3×100 mL)
  3. washThe Combined organic was washed with Brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solid was filtered
  6. washwashed with EtOAc
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7de7aa2432164d1381daeb9b4ad6bda6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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