Dimethylformamide → N-Methyl-N-(2-(3-chloro-4-methoxyphenyl)ethyl)-1,4-diaminobutane

HRID 373938Notes

Reaction equation

HRID 373938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O.[C:29](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:29][N:12]([CH2:11][CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1)[CH2:14][CH2:15][CH2:16][CH2:17][NH2:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 27576442-(3-Chloro-4-methoxyphenyl)ethan-1-amine

Product 1

HCID 19926614N-Methyl-N-(2-(3-chloro-4-methoxyphenyl)ethyl)-1,4-diaminobutaneYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 5.00 g of N-methyl-(2-(3-chloro-4-methoxyphenyl)ethylamine, 9.49 g of N-(4-bromobutyl)phthalimide, 4.16 g of anhydrous potassium carbonate and 50 ml of N,N-dimethylformamide was stirred at a room temperature for 14 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate and the ethyl acetate phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated, followed by the addition of 50 ml of ethanol and 1.5 ml of hydrazine monohydrate. The obtained mixture was heated under reflux for 2 hours, cooled by allowing to stand and filtered to remove insoluble matter. The filtrate was distilled to obtain 3.16 g of the title compound as a colorless oil (yield: 47%).

Workup

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washthe ethyl acetate phase was washed with water
  3. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionfollowed by the addition of 50 ml of ethanol and 1.5 ml of hydrazine monohydrate
  6. temperatureThe obtained mixture was heated
  7. temperatureunder reflux for 2 hours
  8. temperaturecooled
  9. filtrationfiltered
  10. customto remove insoluble matter
  11. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-cdd354a3836647578dbf30cadcfed96b
Source dataset
uspto-grants-1992_11
Patent number
US05166188

Reaction notes

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