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

HRID 419545Notes

Reaction equation

HRID 419545 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.[Na+]>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 336431-IodopropaneHCID 516892Sodium BicarbonateHCID 39674091-(3-Methoxy-4-nitrophenyl)piperazine

Product 1

HCID 598602661-[3-(Methyloxy)-4-nitrophenyl]-4-propylpiperazineYield 35.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[3-(methyloxy)-4-nitrophenyl]piperazine (Example 135, step A) (0.50 g, 2.1 mmol) and 1-iodopropane (0.72 g, 4.22 mmol) was stirred in acetonitrile (42 mL) at rt under N2. To this mixture was added NaHCO3 (0.27 g, 2.5 mmol). The reaction was then heated to reflux and stirred for 24 h. The reaction was cooled to rt, concentrated under vacuum and the residue chromatographed on silica gel to give the title compound of step A (206 mg, 0.74 mmol, 35%) as a yellow oil. MS (ESI): 280 [M+H]+.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. concentrationconcentrated under vacuum
  4. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-48c86d5449d84da390555cdf20b33c31
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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