Triethylamine → 1-(2-Chloro-4-nitrobenzyl)-4-methylpiperazine

HRID 2059799Notes

Reaction equation

HRID 2059799 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[Cl:12].CCN(CC)CC.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][N:24]1[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzene

Product 1

HCID 667358141-(2-Chloro-4-nitrobenzyl)-4-methylpiperazineYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-(bromomethyl)-2-chloro-4-nitro-benzene (29.1 mmol; 50% pure) in 30 mL of DCM was added Et3N (4.2 mL, 30 mmol) and 1-methylpiperazine (3.4 mL, 30 mmol). After stirring for 3 h at ambient temperature, aq. NaHCO3 was added and the mixture was extracted with DCM. The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 5% MeOH/DCM) to provide 6.80 g of product as a dark yellow oil.

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe resulting residue was purified by silica gel chromatography (eluted with 5% MeOH/DCM)

Sources & evidence

ORD record
ord-7b8273bdde414d41ad799996dd6f1c24
Source dataset
uspto-grants-2012_10
Patent number
US08278307B2

Reaction notes

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