Hydrochloric Acid → N-methyl-4-nitrophenethylamine

HRID 24920

Reaction equation

HRID 24920 reaction equation
[CH3:1][NH2:2].Br[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.Cl>ClCCl.O>[CH3:1][NH:2][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 792664-Nitrophenethyl bromide

Product 1

HCID 2794239N-methyl-4-nitrophenethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2.7 g (86 mmol) of methylamine are dissolved in 120 ml of dichloromethane while cooling with ice. 4.9 g (21 mmol) of 4-(2-bromoethyl)-nitrobenzene are added and the mixture is allowed to come up slowly to ambient temperature. After 15 hours stirring the solvent is eliminated in vacuo and the residue taken up in water. An acid pH is created using 2 N hydrochloric acid and the mixture is washed with dichloromethane. The aqueous phase is then adjusted to a basic pH using 4 N sodium hydroxide solution and the product is extracted with dichloromethane.

Workup

  1. temperaturewhile cooling with ice
  2. customto come up slowly to ambient temperature
  3. washthe mixture is washed with dichloromethane
  4. extractionthe product is extracted with dichloromethane

Sources & evidence

ORD record
ord-0770d44e24ec4c24a921ae9eccf562c9
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Linked notes

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