HCID 19420475, compound → 58198-49-5

HRID 863810Notes

Reaction equation

HRID 863810 reaction equation
Br.[N+:2]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)([O-:4])=[O:3]>[OH-].[Na+]>[N+:2]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

3

Reactant 1

HCID 19420475HCID 19420475, compound

Product 1

HCID 9398258198-49-5Yield 78%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Following the procedure of Example 6, but replacing 1-benzylpiperazine with 1-[4-nitrobenzyl]piperazine, provided the desired compound. To a solution of piperazine (2 g, 0.023 mol) in 10 mL of ethanol added a solution of 4-nitrobenzyl bromide (5 g, 0.023 mol) in 20 mL of warm ethanol. It was gently refluxed for 1 hour and stirred at room temperature for one over night. The resulting white precipitate was filtered, washed with a small amount of cold ethanol, and dried to yield 1-[4-nitrobenzyl]piperazine hydrobromide (3 g). MS m/z M+H=222, H1 --NMR (in MeOH-d4) δ=2.7 (t, 4H, piperazine), 3.25 (t, 4H, piperazine), 3.75 (s, 2H, benzyl), 7.62 (d, 2H, aromatic), 8.20 (d, 2H, aromatic). The obtained 1-[4-nitrobenzyl]piperazine hydrobromide (3 g, 9.93 mmol) was dissolved in 60 mL of 3N sodium hydroxide aqueous solution and stirred at room temperature for 30 minutes. The product was extracted with ethyl acetate (50 mL×3), and the combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate. Solvent was removed to obtain 1.7 g of 1-[4-nitrobenzyl]piperazine in 78% yield. MS m/z M+H=222, H1 -NMR (in MeOH-d4) δ=2.45 (t, 4H, piperazine), 2.90 (t, 4H, piperazine), 3.55 (s, 2H, benzyl), 7.52 (d, 2H, aromatic), 8.50 (d, 2H, aromatic).

Workup

  1. extractionThe product was extracted with ethyl acetate (50 mL×3)
  2. washthe combined ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customSolvent was removed

Sources & evidence

ORD record
ord-b9c3d8a53f5342b2a369b09774aeb973
Source dataset
uspto-grants-1996_10
Patent number
US05561140

Reaction notes

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