Piperazine → HCID 19420475, compound

HRID 863809Notes

Reaction equation

HRID 863809 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][Br:15])=[CH:12][CH:11]=1)([O-:9])=[O:8]>C(O)C>[BrH:15].[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 19420475HCID 19420475, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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. temperatureIt was gently refluxed for 1 hour
  2. filtrationThe resulting white precipitate was filtered
  3. washwashed with a small amount of cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-8f03e1e8f0164fe08bc19d96ee59cbbd
Source dataset
uspto-grants-1996_10
Patent number
US05561140

Reaction notes

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