4-Nitrobenzyl chloride → 1-Methyl-4-(4-nitrobenzyl)piperazine

HRID 1390986Notes

Reaction equation

HRID 1390986 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(O)CO>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 8471TriethylamineHCID 531671-Methylpiperazine

Product 1

HCID 6777951-Methyl-4-(4-nitrobenzyl)piperazineYield 59%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of p-nitrobenzyl chloride (5.2 g, 10mM) and 3.2 g of triethylamine in 30 ml of ethylene glycol is added a solution of N-methylpiperazine (3 g, 30 mM) in 20 ml of ethylene glycol. After complete addition, the resulting solution is heated to 80° C. under nitrogen for 30 minutes. The reaction mixture is quenched into aqueous 10% sodium carbonate solution and extracted with methylene chloride. The methylene chloride solution is washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give 4.15 g (59%) of 1-methyl-4-[(4-nitrophenyl)methyl]piperazine.

Workup

  1. additionAfter complete addition
  2. customThe reaction mixture is quenched into aqueous 10% sodium carbonate solution
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution is washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed8dd43d39db427fa67a4c30aaab118a
Source dataset
uspto-grants-1979_02
Patent number
US04140775

Reaction notes

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