N-Methylcyclohexylamine → N-cyclohexyl-N-methyl-N-(4-nitrobenzyl)amine

HRID 1277218Notes

Reaction equation

HRID 1277218 reaction equation
[CH:1]1([NH:7][CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C=O)C>[CH:1]1([N:7]([CH3:8])[CH2:22][C:21]2[CH:24]=[CH:25][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 757291N-cyclohexyl-N-methyl-N-(4-nitrobenzyl)amineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (50 ml) was dissolved N-cyclohexyl-N-methylamine (12.5 g, 0.11 mol), and to the solution were added potassium carbonate (27.6 g, 0.20 mol) and 4-nitrobenzylbromide (21.6 g, 0.10 mol). The mixture was stirred at room temperature for 5 hours. Under reduced pressure, the reaction mixture was concentrated. To the residue was added ethyl acetate, and the mixture was extracted with water. The ethyl acetate layer was washed with saturated sodium chloride solution, dried with MgSO4 and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give N-cyclohexyl-N-methyl-N-(4-nitrobenzyl)amine (24.8 g).

Workup

  1. concentrationUnder reduced pressure, the reaction mixture was concentrated
  2. additionTo the residue was added ethyl acetate
  3. extractionthe mixture was extracted with water
  4. washThe ethyl acetate layer was washed with saturated sodium chloride solution
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7071521d906f4e12a2fd446c85f8a241
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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