Triethylamine → 1-Ethyl-4-(2-methyl-4-nitro-benzyl)-piperazine

HRID 469838Notes

Reaction equation

HRID 469838 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH3:12].[CH2:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14].C(N(CC)CC)C>ClCCl>[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[CH3:12])[CH2:17][CH2:16]1)[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 791961-EthylpiperazineHCID 126541471-(Bromomethyl)-2-methyl-4-nitrobenzene

Product 1

HCID 674579961-Ethyl-4-(2-methyl-4-nitro-benzyl)-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 g (3.78 mmol) 1-bromomethyl-2-methyl-4-nitro-benzene, 0.539 ml (4.16 mmol) 1-ethylpiperazine and 0.63 ml (4.54 mmol) triethylamine in 15 ml dichloromethane is stirred at room temperature for 0.5 h. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, 100% EtOAc=>EtOAc:MeOH=7:3) to afford the title compound as a solid.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic layers are washed with water and saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by chromatography (silicagel, 100% EtOAc=>EtOAc:MeOH=7:3)

Sources & evidence

ORD record
ord-8b37891adf07410fa7861fde38845bf9
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

Loading…