4-Fluorobenzyl chloride → (r)-1-(4-Fluorobenzyl)-3-methylpiperazine

HRID 11624

Reaction equation

HRID 11624 reaction equation
[CH3:1][C@@H: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]Cl)=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:6]2[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 516892Sodium BicarbonateHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 11600914(r)-1-(4-Fluorobenzyl)-3-methylpiperazineYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-2-methyl-piperizine (4.5 g, 45 mmol) in ethanol (80 mL) was added 4-fluorobenzyl chloride (5.38 mL, 45.0 mmol) and sodium hydrogen carbonate (11.3 g, 135 mmol). The reaction was refluxed overnight, cooled and concentrated. The remaining residue was diluted with dichloromethane and washed with water. The organic layer was separated and concentrated to give a clear oil. Chromatography on silica gel gave the title compound (5.0 g).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. temperaturecooled
  3. concentrationconcentrated
  4. additionThe remaining residue was diluted with dichloromethane
  5. washwashed with water
  6. customThe organic layer was separated
  7. concentrationconcentrated
  8. customto give a clear oil

Sources & evidence

ORD record
ord-47c853a443844d0ebba44d6152144a8d
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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