2-Methylpiperazine → 1-(4-Fluorobenzyl)-3-methylpiperazine

HRID 915802Notes

Reaction equation

HRID 915802 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1>C(Cl)Cl>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:6]2[CH2:5][CH2:4][NH:3][CH:2]([CH3:1])[CH2:7]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 680214-Fluorobenzyl bromide

Product 1

HCID 107035841-(4-Fluorobenzyl)-3-methylpiperazineYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methylpiperazine (0.10 g, 1 mmol) in CH2Cl2 (2 mL) was added 4-fluorobenzyl bromide (0.125 mL, 1 mmol). The resultant mixture was stirred at ambient temperature. After 15 hours, the mixture was concentrated in vacuo to afford a solid. This solid was dissolved in CH2Cl2 and washed sequentially with water, aqueous NaHCO3 solution, then brine. The organic layer was dried over MgSO4, filtered, and concentrated to an oil. Purification by flash column chromatography afforded 0.025 g (12% yield) of 1-(4-fluorobenzyl)-3-methylpiperazine, a compound of formula (C), as a colorless oil; NMR (CDCl3) 7.3 (m, 2), 7.0 (m, 2), 3.4 (s, 2), 3.0-2.6 (m, 5), 2.0 (br s, 2), 1.6 (t, 1), 1.0 (d, 3) ppm.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto afford a solid
  3. washwashed sequentially with water, aqueous NaHCO3 solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-30bbacaeed29470db79de169028e1c53
Source dataset
uspto-grants-2007_09
Patent number
US07268140B2

Reaction notes

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