1-Methylpiperazine → 1-Methyl-4-[(2-methyl-3-nitrophenyl)methyl]piperazine

HRID 502720Notes

Reaction equation

HRID 502720 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 108947alpha-Chloro-2-methyl-3-nitrotolueneHCID 516892Sodium Bicarbonate

Product 1

HCID 594279041-Methyl-4-[(2-methyl-3-nitrophenyl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

2-Methyl-3-nitrobenzylchloride (1.0 g, 5.4 mmol) was dissolved in 30 ml of THF, and to this was added 1-methylpiperazine (0.65 g, 6.5 mmol) and sodium bicarbonate (2.26 g, 26.9 mmol). The reaction mixture was stirred at 65° C. for 16 hours. The mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with saturated NH4Cl, H2O, brine and dried over MgSO4. Solvent evaporation afforded 1-(2-methyl-3-nitrobenzyl)-4-methylpiperazine.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with saturated NH4Cl, H2O, brine
  4. dry with materialdried over MgSO4
  5. customSolvent evaporation

Sources & evidence

ORD record
ord-75606caff1cd4d209f83f752c715961d
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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