1-Benzylpiperazine → 1-Benzyl-4-(2-methyl-4-pyridinyl)piperazine

HRID 1162355Notes

Reaction equation

HRID 1162355 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 5813924-Chloro-2-methylpyridine

Product 1

HCID 231382661-Benzyl-4-(2-methyl-4-pyridinyl)piperazineYield 97.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-benzylpiperazine (6.8 g) and 4-chloro-2-methylpyridine (4.9 g) in acetic acid (20 ml) was heated under reflux for 15 hours, and then concentrated under reduced pressure. The residue was dissolved in water, and the reaction mixture was basified with potassium carbonate and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate) to obtain the title compound as a brown oil (10 g, quantitative).

Workup

  1. temperatureunder reflux for 15 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified with basic silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-a7d13996831047ffbd4391c39066fd29
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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