Methanol → N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine

HRID 2236929Notes

Reaction equation

HRID 2236929 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[CH2:12]([N:14]([CH2:17]C)CC)[CH3:13].[CH3:19][OH:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1>[CH3:19][O:20][CH2:13][CH2:12][N:14]([CH3:17])[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 23507717N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 1-bromomethyl-4-nitro-benzene (86.4 mg, 0.4 mmol) in tetrahydrofuran (800 μL) is added triethylamine (200 μL) and 2-(methoxyethyl)methylamine (43 μL, 0.4 mmol). The reaction mixture is shaken at 50° C. for 5 hours. To the reaction mixture is then added 500 μL each of tetrahydrofuran and methanol followed by 350 mg of PS-Ph3P resin to remove unreacted alkyl bromide and shaken for 1 h. The resin is filtered off, rinsed with dichloromethane and the filtrate concentrated. To the residue is added 500 μL each of tetrahydrofuran and methanol followed by 350 mg of PS-TsOH resin to remove unreacted amine. This is then shaken for two hours, filtered, washed with dichloromethane, and concentrated to yield (2-methoxy-ethyl)-methyl-(4-nitro-benzyl)-amine, which is used as such for the subsequent reaction.

Workup

  1. customto remove unreacted alkyl bromide
  2. stirringshaken for 1 h
  3. filtrationThe resin is filtered off
  4. washrinsed with dichloromethane
  5. concentrationthe filtrate concentrated
  6. additionTo the residue is added 500 μL each of tetrahydrofuran and methanol
  7. customto remove unreacted amine
  8. stirringThis is then shaken for two hours
  9. filtrationfiltered
  10. washwashed with dichloromethane
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-df1ca67df8584f98891784201a117c4e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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