Piperazine → 3-Methylbenzylpiperazine

HRID 2379681Notes

Reaction equation

HRID 2379681 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1C=CC=CC=1.C(OCC)C>[CH3:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 12099m-Xylyl bromide

Product 1

HCID 792133-MethylbenzylpiperazineYield 78.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

α-Bromo-m-xylene (10 ml, 74 mmole) was added to a solution of 75 g (11.8 equiv.) of anhydrous piperazine in 500 ml of benzene and the reaction was heated to reflux for two hours. After cooling to room temperature, the reaction was diluted with 300 ml of diethyl ether and washed with 500 ml of 0.2M sodium hydroxide followed by two 500 ml portions of water. The organic solution was dried over sodium sulfate and the solvent removed to give 11.0 g (78%) of crude 1-(3-methylbenzyl)piperazine as a colorless oil.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for two hours
  3. washwashed with 500 ml of 0.2M sodium hydroxide
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-2acf3d57b6d446d6aa6834b7491257be
Source dataset
uspto-grants-1994_11
Patent number
US05364843

Reaction notes

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