HCID 19420474, compound → 1-[(Naphthalen-1-yl)methyl]piperazine

HRID 863811Notes

Reaction equation

HRID 863811 reaction equation
Br.[C:2]1([CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1>[OH-].[Na+]>[C:2]1([CH2:12][N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 19420474HCID 19420474, compound

Product 1

HCID 7018911-[(Naphthalen-1-yl)methyl]piperazineYield 75%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Following the procedure of Example 6, but replacing 1-benzylpiperazine with 1-β-naphthylmethylpiperazine, provided the desired compound. To a solution of piperazine (2.0 g, 0.023 mol) in 15 mL of ethanol added a solution of (2-bromomethyl)naphthalene (5 g, 0.023 mol) in 15 mL of warm ethanol. It was stirred at 55° C. for 1 hour and stirred at room temperature for one over night. The resulting precipitate was filtered, washed with ethyl acetate (20 mL×2), and dried to yield 1-naphthylmethylpiperazine hydrobromide (2.3 g). MS m/z M+H=227, H1 -NMR (in MeOH-d4) δ=2.85 (t, 4H, piperazine), 3.20 (t, 4H, piperazine), 3.72 (s, 2H, benzyl), 7.45 (m, 3H, aromatic), 7.70 (s, 2H, aromatic), 7.80 (3, 3H, aromatic). The obtained 1-naphthylmethylpiperazine hydrobromide (2.2 g, 7.16 mmol) was dissolved in 50 mL of 3 N 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 1.2 g of 1-[naphthylmethyl]piperazine in 75% yield. MS m/z M+H=227, H1 -NMR (in MeOH-d6) δ=2.5 (m, 4H, piperazine), 2.95 (t, 4H, piperazine), 3.55 (s, 2H, benzyl), 7.74 (m, 3H, aromatic), 7.72 (s, 2H, aromatic), 7.79 (m, 3H, 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-57662eea807f4a92a6369ddc880d4df8
Source dataset
uspto-grants-1996_10
Patent number
US05561140

Reaction notes

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