Potassium Carbonate → 1-[3-(Methyloxy)-4-nitrophenyl]-4-propylpiperazine

HRID 1014205Notes

Reaction equation

HRID 1014205 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].I[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 39674091-(3-Methoxy-4-nitrophenyl)piperazine

Product 1

HCID 598602661-[3-(Methyloxy)-4-nitrophenyl]-4-propylpiperazineYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[3-(methyloxy)-4-nitrophenyl]piperazine (1.78 g, 7.51 mmol), 1-iodopropane (1.92 g, 11.3 mmol), and potassium carbonate (4.15 g, 30.0 mmol) in acetonitrile (50 mL) was heated in a pressure vessel at 80° C. for 24 hours. The reaction was cooled and the acetonitrile was removed under reduced pressure. The solids were dissolved in methylene chloride/water. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure. The resultant residue was purified by chromatography on SiO2 (10% MeOH/CH2CL2 with 0.2% NH3) to give 1-[3-(methyloxy)-4-nitrophenyl]-4-propylpiperazine as a pale yellow solid (1.5 g, 5.4 mmol, 72% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.94 (t, J=7.32 Hz, 3H), 1.51-1.61 (m, 2 H), 2.34-2.42 (m, 2 H), 2.59 (s, 4 H), 3.38-3.45 (m, 4 H), 3.95 (s, 3 H), 6.31 (d, J=2.20 Hz, 1 H), 6.42 (dd, J=9.34, 2.38 Hz, 1 H), 8.00 (d, J=9.52 Hz, 1 H).

Workup

  1. temperatureThe reaction was cooled
  2. customthe acetonitrile was removed under reduced pressure
  3. dissolutionThe solids were dissolved in methylene chloride/water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe resultant residue was purified by chromatography on SiO2 (10% MeOH/CH2CL2 with 0.2% NH3)

Sources & evidence

ORD record
ord-9b57210ebf0f45afa3d914c9e44f6e24
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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